Online citations, reference lists, and bibliographies.
← Back to Search

Recent Advances In The Chemoselective Reduction Of Functional Groups Mediated By Samarium(II) Iodide: A Single Electron Transfer Approach.

M. Szostak, M. Spain, D. Procter
Published 2013 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
Recently, samarium(II) iodide reductants have emerged as powerful single electron donors for the highly chemoselective reduction of common functional groups. Complete control of the product formation can be achieved on the basis of a judicious choice of a Sm(II) complex/proton donor couple, even in the presence of extremely sensitive functionalities (iodides, aldehydes). In most cases, the reductions are governed by thermodynamic control of the first electron transfer, which opens up new prospects for unprecedented transformations via radical intermediates under mild regio-, chemo- and diastereoselective conditions that are fully orthogonal to hydrogenation or metal-hydride mediated processes.
This paper references
10.1021/JA049161J
The role of ligand displacement in SmII-HMPA-based reductions.
E. Prasad (2004)
10.1016/S0040-4039(97)00008-7
Electrochemical investigation of the reducing power of SmI2 in THF and the effect of HMPA cosolvent
Masangu Shabangi (1997)
10.1021/JA00050A088
Ring-opening metathesis polymerization of substituted bicyclo[2.2.2]octadienes : a new precursor route to poly(1,4-phenylenevinylene)
V. Conticello (1992)
10.1021/JA00528A029
Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents
P. Girard (1980)
10.1002/anie.201201065
Beyond samarium diiodide: vistas in reductive chemistry mediated by lanthanides(II).
M. Szostak (2012)
10.1016/J.TET.2009.09.111
Toluates: unexpectedly versatile reagents
Kevin Lam (2009)
10.1016/S0040-4039(01)81364-2
Lanthanides in organic synthesis. Synthesis of bicyclicalcohols.
G. Molander (1984)
10.1246/CL.1991.893
Novel reduction of carboxylic acids with samarium diiodide
Y. Kamochi (1991)
10.1002/anie.200803655
Enantioselective synthesis of the core of banyaside, suomilide, and spumigin HKVV.
C. Schindler (2008)
10.1021/JA0475398
N-Boc-L-valine-connected amidomonophosphane rhodium(I) catalyst for asymmetric arylation of N-tosylarylimines with arylboroxines.
M. Kuriyama (2004)
10.1021/JA950937D
Reactions of SmI2 with Olefins: Mechanism and Complexation Effect on Chemoselectivity
Avihai Yacovan (1996)
10.1016/0925-8388(93)90229-G
Samarium-mediated acyclic stereoselection in a radical reaction
J. Inanaga (1993)
10.1016/J.TET.2009.04.053
Second-generation synthesis of salvinorin A
H. Hagiwara (2009)
10.1016/S0040-4039(00)78510-8
Reductive cleavage of CS bond by samarium diiodide: A novel method for the synthesis of disulfides and thiolesters
X. Jia (1994)
10.1039/B500566C
Asymmetric conjugate reductions with samarium diiodide: asymmetric synthesis of (2S,3R)- and (2S,3S)-[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)-[2-(2)H,3-2H]-phenylalanine methyl ester.
S. Davies (2005)
10.1016/0040-4039(91)80819-R
Reduction using samarium diiodide-base system
Y. Kamochi (1991)
10.1002/ANIE.200300583
Strained heterocycles in radical chemistry.
A. Gansäuer (2003)
10.1021/OL0523392
Photoinduced metalation of nonactivated C-Cl bonds with samarium diiodide: synthesis of alkenes with high (Z)-selectivity through beta-elimination reactions.
J. M. Concellón (2005)
10.1055/S-0032-1316840
The Electron-Way: Metal-Catalyzed Reductive Umpolung Reactions of Saturated and α,β-Unsaturated Carbonyl Derivatives
Jan Streuff (2013)
10.1039/c2ob00017b
A general electron transfer reduction of lactones using SmI2-H2O.
M. Szostak (2012)
10.1021/JO035709D
SmI2-Mediated Reduction of γ,γ-Difluoro-α,β-enoates with Application to the Synthesis of Functionalized (Z)-Fluoroalkene-Type Dipeptide Isosteres
A. Otaka (2004)
10.1016/0040-4020(96)00635-7
Some novel electron transfer mediated cascade ring-opening reactions of bicyclo[4.1.0]ketones
R. Batey (1996)
10.1002/anie.201303178
Uncovering the Importance of Proton Donors in TmI2-Promoted Electron Transfer: Facile C−N Bond Cleavage in Unactivated Amides**
M. Szostak (2013)
10.1021/JO052268K
Estimating the limiting reducing power of SmI2/H2O/amine and YbI2/H2O/amine by efficient reduction of unsaturated hydrocarbons.
Anders Dahlén (2006)
10.1016/J.TETLET.2007.05.105
Instantaneous SmI2/H2O/amine mediated reduction of nitroalkanes and α,β-unsaturated nitroalkenes
T. Ankner (2007)
10.1021/ja104480g
Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.
U. Tambar (2010)
10.1016/S0040-4039(01)93404-5
Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol
K. Feldman (1989)
10.1021/ol800944p
Using toluates as simple and versatile radical precursors.
Kevin Lam (2008)
10.1021/ol401265a
Control of transient aluminum-aminals for masking and unmasking reactive carbonyl groups.
Francis J. Barrios (2013)
10.1002/anie.200901317
Chemoselectivity and the curious reactivity preferences of functional groups.
Nicholas A. Afagh (2010)
10.1039/c2cc37772a
A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxides cycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (±)-diospongin A.
H. Yao (2013)
10.1016/0040-4039(95)01474-V
Reduction of azides to amines by samarium diiodide
L. Benati (1995)
10.1002/EJIC.200400309
Microwave‐Assisted Generation of Lanthanide(II) Halides in THF and Simple Quantitative Determination
Anders Dahlén (2004)
10.1021/OL051623Q
Reduction of benzophenone by SmI2: the role of proton donors in determining product distribution.
Gregory Kleiner (2005)
10.1016/J.JALLCOM.2004.12.085
A highly efficient reduction of group 14 heteroatom-chlorine single bonds by using samarium diiodide-mediated reaction systems
I. Kamiya (2006)
10.1021/JO971039Y
Synthesis of Substituted Bicyclo[2.2.2]octatrienes
M. W. Wagaman (1997)
10.1002/anie.201100145
Selective reduction of carboxylic acid derivatives by catalytic hydrosilylation.
D. Addis (2011)
10.1002/anie.201306484
Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts**
M. Szostak (2013)
10.1002/EJOC.200500771
Reduction of Multiple Bonds without Hydrogen or Hydride Complexes: Samarium Diiodide as a Mild Reducing Reagent
J. M. Concellón (2006)
10.1002/anie.200904754
Anodic oxidation and organocatalysis: direct regio- and stereoselective access to meta-substituted anilines by alpha-arylation of aldehydes.
K. L. Jensen (2010)
10.1080/00397919408011736
Aromatic Nucleophilic Substitution by Arylselenolate Ions Produced Through Reductive Cleavage of Diaryl Diselenide Induced by SmI2-THF-HMPA System
W. Bao (1994)
10.1021/jo300135v
Preparation of samarium(II) iodide: quantitative evaluation of the effect of water, oxygen, and peroxide content, preparative methods, and the activation of samarium metal.
M. Szostak (2012)
10.1039/c0cc02009e
Selective α-defluorination of polyfluorinated esters and amides using SmI2/Et3N/H2O.
Jenny Wettergren (2010)
10.1016/S0040-4039(00)01187-4
Synthesis of a molecular tripod to anchor molecular coordination compounds to semiconductor nanoparticles
W. Guo (2000)
10.1002/ANIE.200502015
Total synthesis of (+)-apiosporamide: assignment of relative and absolute configuration.
D. Williams (2005)
10.1021/jo900369t
Efficient diastereoselective synthesis of trifarane-type sesquiterpenes, trifarienols A and B.
Kazunori Takahashi (2009)
10.1021/OL0161514
N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (+/-)-desmethylamino FR901483.
D. Wardrop (2001)
10.1016/0040-4020(81)85053-3
Divalent lanthanide derivatives in organic synthesis—II: Mechanism of SmI2 reactions in presence of ketones and organic halides
H. Kagan (1981)
10.1016/S0040-4020(99)00486-X
Reductive cleavage of NO bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide
G. E. Keck (1999)
10.1021/JA00132A047
TOTAL SYNTHESIS OF (+)-7-DEOXYPANCRATISTATIN : A RADICAL CYCLIZATION APPROACH
G. E. Keck (1995)
10.1021/ja9013997
Guidelines for the use of proton donors in SmI2 reactions: reduction of alpha-cyanostilbene.
Mazal Amiel-Levy (2009)
10.1002/ANIE.200461338
Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines.
T. Hayashi (2004)
10.1021/jo201734t
Chemoselective samarium-mediated benzoyloxysulfone eliminations.
Erasmus O. Volz (2011)
10.1002/EJOC.201101175
Synthesis and Cytotoxicity of Ring C‐Functionalized Derivatives of the Marine Natural Product (–)‐Dibromophakellstatin
Rareş-Petru Moldovan (2012)
10.1055/S-1996-5547
IMPROVED REACTIVITY OF DIIODOSAMARIUM BY CATALYSIS WITH TRANSITION METAL SALTS
Fouzia Machrouhi (1996)
10.1002/EJIC.201300288
Preliminary Theoretical Insights into SmI2-Mediated Reactions: Activation of Ketones in THF
C. Kefalidis (2013)
10.1021/JA0168918
A mechanistic study of the samarium(II)-mediated reduction of aryl nitro compounds to the corresponding crylamines. The crystal structures of [Sm[N(SiMe(3))(2)](2)(thf)](2)(mu(2)-O) and [(Me(3)Si)(2)N](2)Sm(thf)(mu-PhNNPh)Sm[N(SiMe(3))(2)](2).
E. D. Brady (2002)
10.1002/anie.200905490
A dialdehyde cyclization cascade: an approach to pleuromutilin.
M. Helm (2009)
10.1021/JO00086A005
Deprotection of Arenesulfonamides with Samarium iodide
E. Vedejs (1994)
10.1002/EJOC.201200304
Indium-Mediated Aza-Henry Reaction of Imines: Access to 2-Nitroamines
R. Soengas (2012)
10.1021/JA028111G
Investigation of the [Sm(N(SiMe(3))(2))(2)] reducing system in THF. Rate and mechanistic studies.
E. Prasad (2002)
10.1016/S0040-4039(03)00369-1
Selective reduction of carboncarbon double and triple bonds in conjugated olefins mediated by SmI2/H2O/amine in THF
Anders Dahlén (2003)
10.1016/S0040-4020(01)00079-5
Efficient preparation of trisubstituted alkenes using the SmI2 modification of the Julia-Lythgoe olefination of ketones and aldehydes
I. Markó (2001)
10.1021/OL0344063
A transient N-O-linked Pauson-Khand strategy for the synthesis of the deschloro carbocyclic core of the palau'amines and styloguanidines.
Stefan G Koenig (2003)
10.1021/JA074939X
On the structure of palau'amine: evidence for the revised relative configuration from chemical synthesis.
B. A. Lanman (2007)
10.1246/CL.1987.1485
A Mild and Convenient Method for the Reduction of Organic Halides by Using a SmI2-THF Solution in the Presence of Hexamethylphosphoric Triamide (HMPA)
J. Inanaga (1987)
10.1016/J.TETLET.2009.02.025
SmI2-mediated dialdehyde cyclization cascades
M. Helm (2009)
10.1021/JA069371R
Direct access to N-H-aziridines from asymmetric catalytic aziridination with borate catalysts derived from vaulted binaphthol and vaulted biphenanthrol ligands.
Zhenjie Lu (2007)
10.1002/chem.201003489
Development of a flexible strategy towards FR900482 and the mitomycins.
B. Trost (2011)
10.1039/B606111G
Samarium enolates and their application in organic synthesis
Iain M. Rudkin (2008)
10.1080/00397919408010610
Reductive Cleavage of S-S Bond by Samarium Diiodide: A Novel Method for the Synthesis of Disulfides
X. Jia (1994)
10.1021/JO048365F
Syntheses of (+)-cytisine, (-)-kuraramine, (-)-isokuraramine, and (-)-jussiaeiine A.
T. Honda (2005)
10.1021/jo302353g
Toward the synthesis of phomoidride D.
G. Murphy (2013)
10.1021/JO982428A
An Especially Convenient Stereoselective Reduction of β-Hydroxy Ketones to Anti 1,3 Diols Using Samarium Diiodide†
G. E. Keck (1999)
10.1021/jo4001492
Flexible synthesis and evaluation of diverse anti-Apicomplexa cyclic peptides.
Mariam Traoré (2013)
10.1002/anie.201103128
Concise syntheses of strychnine and englerin A: the power of reductive cyclizations triggered by samarium iodide.
M. Szostak (2011)
10.1021/JA038363X
The role of proton donors in SmI2-mediated ketone reduction: new mechanistic insights.
P. R. Chopade (2004)
10.1021/ol901269d
A catalytic asymmetric route to carbapenems.
Micah J. Bodner (2009)
10.1021/JA060847G
Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation.
W. D. Shipe (2006)
10.1016/S0003-2670(01)81677-9
Polarographic reduction of pyridinium ion in pyridine tetraethylammonium perchlorate as background electrolyte
Janice E. Hickey (1966)
10.1016/S0040-4039(00)96532-8
SmI2-Induced highly regioselective reduction of α,β-epoxy esters and γ,δ-epoxy-α,β-unsaturated esters. An efficient route to optically active β-hydroxy and δ-hydroxy esters☆
K. Otsubo (1987)
10.1002/ANIE.200462252
Total synthesis of the marine natural product rac-dibromophakellstatin.
D. Jacquot (2005)
10.1021/ja9066354
Tandem asymmetric Aza-Darzens/ring-opening reactions: dual functionality from the silane lewis acid.
S. Valdez (2009)
10.1021/JA00095A074
Samarium(II) Iodide Induced Radical Cyclizations of Halo- and Carbonylhydrazones
C. Sturino (1994)
10.1246/CL.1993.1495
Novel Reduction of Carboxylic Acids, Esters, Amides and Nitriles Using Samarium Diiodide in the Presence of Water.
Y. Kamochi (1993)
Organic Synthesis using Samarium Diiodide: A Practical Guide
D. Procter (2010)
10.1021/IC062011K
The importance of questioning scientific assumptions: some lessons from f element chemistry.
W. Evans (2007)
10.1021/JA076671F
Total synthesis of the maduropeptin chromophore aglycon.
Kazuo Komano (2007)
10.1021/JO061670B
Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis.
J. Geiger (2007)
10.1002/EJIC.200800876
Generation of SmII Reductants Using High Intensity Ultrasound
J. Teprovich (2008)
10.1021/JO00070A046
Additive and solvent effects on samarium diiodide reductions: the effects of water and DMPU
E. Hasegawa (1993)
10.1021/JA962517+
Highly Stereoselective First Synthesis of an A-Ring-Functionalized Bakkane: Novel Free-Radical Approach to 9-Acetoxyfukinanolide
O. Hamelin (1996)
10.1021/jo802547r
Reduction of benzophenones with SmI2. Post electron transfer processes.
H. Farran (2009)
10.1002/anie.200805518
Total synthesis of a protected aglycon of the kedarcidin chromophore.
Kouki Ogawa (2009)
10.1002/1521-3773(20001201)39:23<4314::AID-ANIE4314>3.0.CO;2-Q
The First Entry to Complex Bakkanes: A Highly Effective Retroaldol-Aldol-Based Approach to (-)-Bakkenolides III, B, C, and H.
O. Hamelin (2000)
10.1021/OL0160957
Influence of HMPA on reducing power and reactivity of SmBr(2).
B. W. Knettle (2001)
10.1021/JA963117P
Photoinduced Reduction and Carbonylation of Organic Chlorides with Samarium Diiodide
A. Ogawa (1997)
10.1016/S0040-4039(00)85559-8
Selective reduction of isoxazoles with samarium diiodide
N. Natale (1982)
10.1039/b814595d
Secure route to the epoxybicyclo[7.3.0]dodecadienediyne core of the kedarcidin chromophore.
Kouki Ogawa (2008)
10.1016/J.TET.2010.09.025
Synthesis of substituted ( S )-2-aminotetralins via ring-opening of aziridines prepared from l-aspartic acid β- tert -butyl ester
Jon Erik Aaseng (2010)
10.1021/JO00123A041
Protection of Amines by the Pyridine-2-sulfonyl Group and Its Cleavage under Mild Conditions (SmI2 or Electrolysis)
C. Goulaouic‐Dubois (1995)
10.1021/JA063304F
Strain-release rearrangement of N-vinyl-2-arylaziridines. Total synthesis of the anti-leukemia alkaloid (-)-deoxyharringtonine.
J. D. Eckelbarger (2006)
10.1021/JO034173T
Rapid SmI2-mediated reductions of alkyl halides and electrochemical properties of SmI2/H2O/amine.
Anders Dahlén (2003)
10.1016/0166-1280(82)80171-1
Le calcul de l'energie de stabilisation des especes chimiques
G. Leroy (1982)
10.1016/S0040-4039(00)01434-9
Aggregation state and reducing power of the samarium diiodide–DMPU complex in acetonitrile
Matthew L. Kuhlman (2000)
10.1016/0040-4039(94)88314-9
A simple synthesis of 10-deacetoxytaxol derivatives
R. Holton (1994)
10.1021/ja804624u
Enantioselective total syntheses of nankakurines A and B: confirmation of structure and establishment of absolute configuration.
B. Nilsson (2008)
10.1021/JO00126A005
REDUCTION OF 2-ACYLAZIRIDINES BY SAMARIUM(II) IODIDE. AN EFFICIENT AND REGIOSELECTIVE ROUTE TO BETA -AMINO KETONES AND ESTERS
G. Molander (1995)
10.1016/S0040-4039(00)99165-2
A highly efficient deoxygenation of α-oxygenated esters via SmI2-induced electron transfer process
K. Kusuda (1989)
10.1021/ja208873k
Efficient organocatalytic cross-aldol reaction between aliphatic aldehydes through their functional differentiation.
T. Kano (2011)
10.1021/JA00219A035
Directed reduction of .beta.-hydroxy ketones employing tetramethylammonium triacetoxyborohydride
D. A. Evans (1988)
10.1039/B712841J
A versatile strategy for the synthesis of N-linked glycoamino acids from glycals.
V. Kumar (2007)
10.1021/jo102566e
Synthesis of mono- and 1,3-diaminocalix[4]arenes via Ullmann-type amination and amidation of 1,3-bistriflate esters of calix[4]arenes.
Y. Nakamura (2011)
10.1016/S0040-4039(97)10222-2
The effect of lithium bromide and lithium chloride on the reactivity of SmI2 in THF
J. R. Fuchs (1997)
10.1016/0040-4039(95)00445-I
Thiocyanate as a versatile synthetic unit: Efficient conversion of ArSCN to aryl alkyl sulfides and aryl thioesters
F. Toste (1995)
10.1021/JO990826N
A Single-Pot, Mild Conversion of β-Lactones to β-Lactams
H. W. Yang (1999)
10.1021/OL049074W
Stereocontrolled total synthesis of potent immunosuppressant FR901483.
T. Kan (2004)
10.1021/ol801743d
Diastereoselective synthesis of alpha,beta'-disubstituted aminomethyl(2-carboxyethyl)phosphinates as phosphinyl dipeptide isosteres.
T. Yamagishi (2008)
10.1002/anie.201200959
Bioinspired total synthesis of agelastatin A.
Jeremy Chris P. Reyes (2012)
10.1016/J.TET.2003.09.101
Twenty-five years of organic chemistry with diiodosamarium: an overview
H. Kagan (2003)
10.1080/00397919508015867
Aromatic Nucleophilic Substitution with Aryltellurolate lons Produced Through Reductive Cleavage of Diaryl Ditellurides by Samarium Diiodide
W. Bao (1995)
10.1248/CPB.53.1017
Facile deoxygenation of dicarbonyl compounds using a samarium diiodide-additive system.
Y. Kamochi (2005)
10.1016/S0040-4039(00)01185-0
Lithium N-trityl-N-(R)-1-phenethylamide, a readily available and useful base for the enantioselective formation of chiral enolates from achiral ketones
J. Busch-Petersen (2000)
10.1021/jo3017555
Collective synthesis of Lycopodium alkaloids and tautomer locking strategy for the total synthesis of (-)-lycojapodine A.
H. Li (2013)
10.1021/ol300188e
Highly chemoselective reduction of carbonyl groups in the presence of aldehydes.
Gulluzar Bastug (2012)
Lanthanides : chemistry and use in organic synthesis
小林 修 (1999)
10.1021/ol801752m
General, stereoselective synthesis of (Z)-beta,gamma-unsaturated nitriles promoted by samarium diiodide.
J. M. Concellón (2008)
10.1038/nchem.1330
Total synthesis of marinomycin A using salicylate as a molecular switch to mediate dimerization.
P. Evans (2012)
10.1021/JO0507542
Synthesis of 2'-C-difluoromethylribonucleosides and their enzymatic incorporation into oligonucleotides.
J. Ye (2005)
10.1039/P19750001574
A new method for the deoxygenation of secondary alcohols
D. Barton (1975)
10.1038/nprot.2012.034
Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O
M. Szostak (2012)
10.1039/A709124I
Reductive Cleavage of the Se–Si Bond in Arylselenotrimethylsilanes: Novel Method for the Synthesis of Unsymmetrical Selenides†
Songlin Zhang (1998)
10.1021/ja400473v
Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer.
James H Frederich (2013)
10.1021/OL026456Y
Directed reduction of beta-amino ketones to syn or anti 1,3-amino alcohol derivatives.
G. E. Keck (2002)
10.1039/B400677A
β-Elimination reactions by using samarium diiodide
J. M. Concellón (2004)
10.1002/anie.200801020
Highly enantioselective zinc/binol-catalyzed alkynylation of N-sulfonyl aldimines.
G. Blay (2008)
10.1021/JA9826688
Total Syntheses of (−)-Lycoricidine, (+)-Lycoricidine, and (+)-Narciclasine via 6-exo Cyclizations of Substituted Vinyl Radicals with Oxime Ethers†
G. E. Keck (1999)
10.1016/J.TETLET.2004.09.050
Samarium(II) iodide reduction of isoxazolidines
J. Revuelta (2004)
10.1002/EJIC.200400442
Samarium(II) Iodide Mediated Reductions − Influence of Various Additives
Anders Dahlén (2004)
10.1021/ol301281s
Enantioselective synthesis of 1-aryl-tetrahydroisoquinolines through iridium catalyzed asymmetric hydrogenation.
F. Berhal (2012)
10.1039/c0ob01229g
A convenient pathway to Sm(II)-mediated chemistry in acetonitrile.
Todd Maisano (2011)
10.1021/OL060755W
Enantioselective rh-catalyzed arylation of N-tosylarylimines with arylboronic acids.
Hai-feng Duan (2006)
10.1021/ol901608k
SmI(2)-mediated carbon-carbon bond fragmentation in alpha-aminomethyl malonates.
Q. Xu (2009)
10.1002/1521-3765(20021004)8:19<4493::AID-CHEM4493>3.0.CO;2-U
Synthesis of different deuterated carboxylic acids from unsaturated acids promoted by samarium diiodide and D2O.
J. M. Concellón (2002)
10.1021/ol800733b
Mn-mediated coupling of alkyl iodides and ketimines: a radical addition route to alpha,alpha-disubstituted alpha-aminoesters.
Gregory K. Friestad (2008)
10.1021/ol900828x
Chemoselective chemical and electrochemical deprotections of aromatic esters.
Kevin Lam (2009)
10.1246/BCSJ.65.3049
Lanthanoids in Organic Synthesis. I. The Novel Reduction of Carboxylic Acids with Samarium Diiodide-Base System
Y. Kamochi (1992)
10.1002/chem.201300968
Total synthesis of (+)-pleuromutilin.
N. Fazakerley (2013)
10.1246/CL.1987.2101
SmI2-Induced Deoxygenation of Epoxides and Its Application to Carbonyl Methylenation in Combination with Iodomethylation
Mihaya Matsukawa (1987)
10.1039/CC9960001805
Novel reduction of isothiocyanates to thioformamides with SmI2 and tert-butyl alcohol in the presence of HMPA
Heui Sul Park (1996)
10.1021/OL0501018
Diastereoselective synthesis of pyrrolidines using a nitrone/cyclopropane cycloaddition: synthesis of the tetracyclic core of nakadomarin A.
I. S. Young (2005)
10.1038/nchem.1096
Generation and exploitation of acyclic azomethine imines in chiral Brønsted acid catalysis
T. Hashimoto (2011)
10.1002/chem.200701998
Synthesis of antiproliferative Cephalotaxus esters and their evaluation against several human hematopoietic and solid tumor cell lines: uncovering differential susceptibilities to multidrug resistance.
J. D. Eckelbarger (2008)
10.1021/JO00115A041
USE OF SAMARIUM DIIODIDE AS AN ALTERNATIVE TO SODIUM/MERCURY AMALGAM IN THE JULIA-LYTHGOE OLEFINATION
G. E. Keck (1995)
10.1016/J.TET.2009.10.086
SmI2/H2O/amine promoted reductive cleavage of benzyl-heteroatom bonds: optimization and mechanism
T. Ankner (2009)
10.3987/REV-10-684
Development of samarium diiodide-promoted reductive carbon-nitrogen bond cleavage reaction of α-amino carbonyl compounds: application to the synthesis of biologically active alkaloids
T. Honda (2011)
10.1021/JA020051R
Mechanistic Study of β-Substituent Effects on the Mechanism of Ketone Reduction by SmI2
E. Prasad (2002)
10.1021/jo101619d
Total synthesis of (+)-nankakurines A and B and (±)-5-epi-nankakurine A.
R. A. Altman (2010)
10.1055/S-2008-1078414
Mechanistic Studies on the Roles of Cosolvents and Additives in Samarium(II)-Based Reductions
R. Flowers (2008)
10.1016/0040-4039(91)85009-T
Reductive desulfonylation of phenyl sulfones by samarium(II) iodide-hexamethylphosphoric triamide
H. Kuenzer (1991)
10.1021/ja204287n
Catalytic Ni(II) in reactions of SmI2: Sm(II)- or Ni(0)-based chemistry?
Kimberly A. Choquette (2011)
10.1016/S0040-4039(00)78431-0
1,3-asymmetric induction in hydride addition reactions to β-substituted ketones. A model for chirality transfer
D. A. Evans (1994)
10.1021/OL006072C
The first directed reduction of beta-alkoxy ketones to anti-1,3-diol monoethers: identification of spectator and director alkoxy groups.
G. E. Keck (2000)
10.1002/ANIE.200290038
Stereoselective total synthesis of mucocin, an antitumor agent.
Shunya Takahashi (2002)
10.1002/EJOC.200210669
Very Rapid Preparation of SmI2 by Sonic Treatment of Iodoform and Metallic Samarium
J. M. Concellón (2003)
10.1016/S0040-4039(00)92313-X
A practical synthesis of 2-deoxy aldonolactones via a SmI2-mediated α-deoxygenation reaction
S. Hanessian (1992)
10.1021/ja807129e
Synthesis of beta-, gamma-, and delta-lactams via Pd(II)-catalyzed C-H activation reactions.
M. Wasa (2008)
10.1246/CL.1990.1141
Samarium diiodide-promoted reductive coupling of imines.
T. Imamoto (1990)
10.1021/ja078137d
A ring size-selective reduction of lactones using SmI2 and H2O.
L. A. Duffy (2008)
10.1039/B408257E
Diastereoselective conjugate reduction with samarium diiodide: asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate.
S. Davies (2004)
10.1021/ja207385y
Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.
Ke Kong (2011)
10.1021/CR9902648
Reagent-controlled transition-metal-catalyzed radical reactions.
A. Gansäuer (2000)
10.1016/J.TETLET.2010.11.078
Synthesis of pseudaminic acid, a unique nonulopyranoside derived from pathogenic bacteria through 6-deoxy-AltdiNAc
Y. Lee (2011)
10.1080/00397919408011197
Reductive Cleavage of S-S Bond in Diphenyl Disulfide by Samarium Diiodide: A Novel Method for the Synthesis of Thiolesters
X. Jia (2006)
10.1021/JA068047T
Total synthesis of (+)-nakadomarin A.
I. S. Young (2007)
10.1016/0040-4020(84)80006-X
Stereoselective reduction of β hydroxyketones to 1,3-diols highly selective 1,3-asymmetric induction via boron chelates
K. Narasaka (1984)
10.1021/JO970367V
SmI2-Promoted Deprotection of N-(Arylsulfonyl)glucosamines
D. Hill (1997)
10.1021/OL302165D
A formal enantioselective total synthesis of FR901483.
Haohua Huo (2012)
10.1021/JO061813U
Total synthesis of the cytostatic marine natural product dibromophakellstatin via three-component imidazolidinone anellation.
M. Zoellinger (2006)
10.1039/B508300A
A formal synthesis of (+)-lactacystin.
D. Wardrop (2005)
10.1055/S-1992-21544
New mechanistic insights into reductions of halides and radicals with samarium(II) iodide
D. Curran (1992)
10.1002/anie.200902151
Samarium diiodide mediated reactions in total synthesis.
K. Nicolaou (2009)
10.1021/OL036480R
Trifluoroacetyl-activated nitrogen-nitrogen bond cleavage of hydrazines by samarium(II) iodide.
H. Ding (2004)
10.1021/JA0204675
Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemine.
F. Ng (2002)
10.1021/jo1023206
The effect of proton donors on the facial stereoselectivity in SmI2 reduction of norcamphor.
S. K. Upadhyay (2011)
10.1002/anie.201201787
Catalytic selective synthesis.
J. Mahatthananchai (2012)
10.1021/ja2047232
Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.
Ian B. Seiple (2011)
10.1021/JO951571Q
Cleavage of N−O Bonds Promoted by Samarium Diiodide: Reduction of Free or N-Acylated O-Alkylhydroxylamines
J. L. Chiara (1996)
10.1002/chem.200900996
Enantiopure aminopyrans by a Lewis acid promoted rearrangement of 1,2-oxazines: versatile building blocks for oligosaccharide and sugar amino acid mimetics.
A. Al-Harrasi (2009)
10.1021/OL049583Y
Pd-catalyzed carbonylative lactamization: a novel synthetic approach to FR900482.
B. Trost (2004)
10.1021/OL047835P
Reduction of β-Hydroxyketones by SmI2/H2O/Et3N
T. Davis (2005)
10.1016/J.TET.2005.11.028
Synthesis of α-diazo-β-hydroxyesters through a one-pot protocol by phase-transfer catalysis: application to enantioselective aldol-type reaction and diastereoselective synthesis of α-amino-β-hydroxyester derivatives
K. Hasegawa (2006)
10.1021/JA00254A051
Total synthesis of (.+-.)-atractyligenin
Ashutosh Kumar Singh (1987)
10.1016/0040-4039(95)01557-4
Reductive cleavage of NO bonds in hydroxylamine and hydroxamic acid derivatives using SmI2/THF
G. E. Keck (1995)
10.3987/COM-93-6476
The novel reduction of pyridine derivatives with samarium diiodide
Y. Kamochi (1993)
10.1021/ol102040s
Tripyrrolidinophosphoric acid triamide as an activator in samarium diiodide reductions.
C. E. McDonald (2010)
10.1021/JA00031A019
Ab initio calculations on potential intermediates in metal reductions of carbonyl compounds. Stereochemical considerations
Yun-Dong Wu (1992)
10.1021/ja2073356
A concise total synthesis of (-)-maoecrystal Z.
Jacob Y. Cha (2011)
10.1039/c1cc14014k
Electron transfer reduction of unactivated esters using SmI2-H2O.
M. Szostak (2011)
10.2533/chimia.2012.399
Recent advances in the chemistry of SmI(2)-H(2)O.
B. Sautier (2012)
10.1016/S0040-4039(98)00839-9
The effect of cosolvent on the reducing power of SmI2 in tetrahydrofuran
Masangu Shabangi (1998)
10.1039/c3cc41642a
Selective cleavage of 3,5-bis-(trifluoromethyl)benzylcarbamate by SmI2-Et3N-H2O.
T. Ankner (2013)
10.1039/A807448H
Photochemical reactions of chiral 2,3-dihydro-4(1H)-pyridones: asymmetric synthesis of (–)-perhydrohistrionicotoxin
D. Comins (1998)
10.1002/1521-3765(20011001)7:19<4266::AID-CHEM4266>3.0.CO;2-8
Sequential elimination-reduction reactions promoted by samarium diiodide: synthesis of 2,3-dideuterioesters or -amides.
J. M. Concellón (2001)
10.1002/CHEM.200401320
Exploring SmBr2-, SmI2-, and YbI2-mediated reactions assisted by microwave irradiation.
Anders Dahlén (2005)
10.1016/S0040-4020(01)80441-5
Reductions of carboxylic acids and their derivatives using samarium diiodide-acid system
Y. Kamochi (1992)
10.1016/J.TETLET.2004.01.051
Deuteration of α, β-acetylenic esters, amides, or carboxylic acids without using deuterium gas: synthesis of 2,2,3,3-tetradeuterioesters, amides, or acids
J. M. Concellón (2004)
10.1021/CR950019Y
Sequencing Reactions with Samarium(II) Iodide.
G. Molander (1996)
10.1021/JO00029A010
The regioselective cleavage of aryl tosylates by electrochemical reduction
E. Civitello (1992)
10.1021/AR020230D
Bond dissociation energies of organic molecules.
S. Blanksby (2003)
10.1002/1521-3765(20001016)6:20<3747::AID-CHEM3747>3.0.CO;2-B
Evidence for ionic samarium(II) species in THF/HMPA solution and investigation of their electron-donating properties
Enemaerke (2000)
10.1021/ol2010598
Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via type II anion relay chemistry.
A. Smith (2011)
10.1016/0040-4039(95)80003-4
Efficient reduction of azides with samarium diiodide
C. Goulaouic‐Dubois (1995)
10.1021/JA001260J
Reactions of SmI2 with Alkyl Halides and Ketones: Inner-Sphere vs Outer-Sphere Electron Transfer in Reactions of Sm(II) Reductants
R. S. Miller (2000)
10.1021/JM030302M
Neurosteroid Analogues. 9. Conformationally Constrained Pregnanes: Structure−Activity Studies of 13,24-Cyclo-18,21-dinorcholane Analogues of the GABA Modulatory and Anesthetic Steroids (3α,5α)- and (3α,5β)-3-Hydroxypregnan-20-one
X. Jiang (2003)
10.1039/A903073E
Reductive deamination of α-amino carbonyl compounds by means of samarium iodide
T. Honda (1999)
Reductions in organic chemistry
M. Hudlický (1984)
10.1039/A908189E
Recent developments in lanthanide mediated organic synthesis
P. Steel (2001)
10.1002/1521-3773(20011015)40:20<3897::AID-ANIE3897>3.0.CO;2-O
Synthesis of Isotopically Labeled (E)-β,γ-Unsaturated Esters with Total or High Diastereoselectivity by Using Samarium Diiodide.
J. M. Concellón (2001)
10.1039/C39890000298
Rapid and mild deoxygenation of organoheteroatom oxides with the efficient electron transfer system SmI2–tetrahydrofuran–hexamethylphosphoric triamide
Y. Handa (1989)
10.1016/S0040-4020(00)00025-9
Desulfonylation of Amides using Tributyltin Hydride, Samarium Diiodide or Zinc/Titanium Tetrachloride. A Comparison of Methods
Haydn S Knowles (2000)
10.1021/ja901715d
Selective reductions of cyclic 1,3-diesters using SmI(2) and H(2)O.
Giuditta Guazzelli (2009)
10.1021/jo1003295
Enantioselective chemoenzymatic synthesis of cis- and trans-2,5-disubstituted morpholines.
B. Ritzen (2010)
10.1016/S0040-4039(02)01673-8
Instantaneous SmI2–H2O-mediated reduction of dialkyl ketones induced by amines in THF
Anders Dahlén (2002)
10.1021/CR980326E
Coupling of Organic Halides with Carbonyl Compounds Promoted by SmI(2), the Kagan Reagent.
A. Krief (1999)
10.1021/ol802243d
Instantaneous deprotection of tosylamides and esters with SmI(2)/amine/water.
T. Ankner (2009)
10.1039/c1ob05710c
Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds.
S. C. Coote (2011)
10.1021/JO990695Q
2-Naphthalenesulfonyl as a Tosyl Substitute for Protection of Amino Functions. Cyclic Voltammetry Studies on Model Sulfonamides and Their Preparative Cleavage by Reduction†
B. Nyasse (1999)
10.1016/S0040-4039(00)79824-8
A new route to 1,1-difluoro olefins: Application to the synthesis of 2′-deoxy-2′-difluoromethylene nucleosides.
J. Sabol (1992)
10.1039/C2SC20171B
Catalytic asymmetric α-amination of carboxylic acids using isothioureas
Louis C Morrill (2012)
10.1016/S0040-4020(97)90399-9
Reduction of 2-acylaziridines by samarium(II) iodide. An efficient and regioselective route to β-amino carbonyl compounds
G. Molander (1997)
10.1016/S0957-4166(02)00586-4
Asymmetric synthesis of amathamides A and B: novel alkaloids isolated from Amathia wilsoni
Moisés Ramı́rez Osuna (2002)
10.1002/anie.201200205
Synthetic (±)-axinellamines deficient in halogen.
Hui Ding (2012)
10.1039/c0cs00116c
Samarium diiodide induced ketyl-(het)arene cyclisations towards novel N-heterocycles.
C. Beemelmanns (2011)
10.1016/S0040-4039(00)74307-3
Controlled reduction of nitroalkanes to alkyl hydroxylamines or amines by samarium diiodide
A. Kende (1991)
10.1021/jo802215v
Total synthesis of epothilones B and D: stannane equivalents for beta-keto ester dianions.
G. E. Keck (2008)
10.1021/ja909870g
Total synthesis of the antimitotic bicyclic peptide celogentin C.
Bing Ma (2010)
10.1021/JA056352T
Mechanistic impact of water addition to SmI2: consequences in the ground and transition state.
E. Prasad (2005)
10.1021/CR030017A
Samarium(II)-iodide-mediated cyclizations in natural product synthesis.
D. Edmonds (2004)
10.1002/anie.200906318
A concise formal synthesis of diazonamide A by the stereoselective construction of the C10 quaternary center.
Cheng-Kang Mai (2010)
10.1016/S0040-4039(00)73141-8
Novel and facile reduction of phenol derivatives with samarium diiodide-base system
Y. Kamochi (1994)
10.1055/S-0029-1216953
Total Synthesis of (+)-Dodoneineand Its 6-Epimer
G. Sabitha (2009)
10.1039/c3cc37828d
Solvent dependent reductive defluorination of aliphatic C-F bonds employing Sm(HMDS)2.
M. Janjetovic (2013)
10.1021/ol203361k
Electron transfer reduction of carboxylic acids using SmI2-H2O-Et3N.
M. Szostak (2012)
10.1016/0022-328X(83)85053-0
Some organic reactions promoted by samarium diiodide
J. Souppe (1983)
10.1021/OL990329T
Mechanism of Reduction of Primary Alkyl Radicals by SmI2−HMPA
Masangu Shabangi (1999)
10.1016/S0040-4039(01)00958-3
Chelating alcohols accelerate the samarium diiodide mediated reduction of 3-heptanone
A. Dahlén (2001)
10.1039/B612151A
Iodine catalyzed one-pot diamination of glycals with chloramine-T: a new approach to 2-amino-beta-glycosylamines for applications in N-glycopeptide synthesis.
V. Kumar (2006)
10.1016/S0040-4039(99)02051-1
Novel and facile selective reduction of carboxylic acid with a samarium diiodide–lanthanide triflate–methanol–base system
Y. Kamochi (2000)
10.1002/ANIE.200501127
Synthesis of enantiopure carbohydrate mimetics by Lewis acid catalyzed rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines.
A. Al-Harrasi (2005)
10.1016/J.TET.2003.06.004
Reduction and reductive coupling of imines by Sm(II)-based reagents
M. Kim (2003)
10.1002/anie.201205260
Synthesis of fluorinated building blocks by transition-metal-mediated hydrodefluorination reactions.
Moritz F Kuehnel (2013)
10.1021/ja1081603
Catalytic enantioselective 1,3-dipolar cycloadditions of nitrones with propioloylpyrazoles and acryloylpyrazoles induced by chiral π-cation catalysts.
A. Sakakura (2010)
10.1021/ja8050487
Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions: use of allylic strain to control product stereochemistry through N-substituent manipulation.
Natalie C. Giampietro (2008)
10.1002/EJOC.201000279
Conversion of Conjugated Enones into Enantiomerically Pure ‐Hydroxy Ketones or 1,3‐Diols – Samarium(II) Bromide Reductions of Protected ,‐Dihydroxy Ketones
Andreas Zoerb (2010)
10.1016/J.TET.2013.02.025
Dipyrrolidinomethylaminophosphoric acid triamide (DPMPA) as an activator for the samarium diiodide-mediated reduction of alkyl and aryl halides
C. E. McDonald (2013)
10.1021/JO00357A040
Lanthanides in organic synthesis. 2. Reduction of .alpha.-heterosubstituted ketones
G. Molander (1986)
10.1021/JO991089Y
Synthesis of a chiral spiranic aminochroman derivative from L-proline.
S. Usse (2000)
10.1016/J.TET.2009.09.035
SmI2-mediated dialdehyde 'radical then aldol' cyclization cascades: a feasibility study
M. Helm (2009)
10.1039/A705190E
REDUCTIVE CLEAVAGE OF THE S-SI BOND IN ARYLSULFANYLTRIMETHYLSILANES : A NOVEL METHOD FOR THE SYNTHESIS OF UNSYMMETRICAL SULFIDES
Songlin Zhang (1998)
10.1016/0040-4039(94)02398-U
Non-toxic ligands in samarium diiodide-mediated cyclizations
W. Cabri (1995)
10.1039/C2SC21651E
Total Synthesis of Ageliferin via Acyl N-amidinyliminium Ion Rearrangement.
Hui Ding (2013)
10.1246/CL.1991.2117
Selective conjugate reduction of α,β-unsaturated esters and amides via SmI2-promoted electron transfer process
J. Inanaga (1991)
10.1055/S-1997-771
Desulfonylation of Amides Using Samarium Iodide
Haydn S Knowles (1997)
10.1002/chem.201000632
Selective reductions of cyclic 1,3-diesters by using SmI(2) and H(2)O.
Karl D. Collins (2010)
10.1039/B009513N
Diastereoselective SmI2 mediated cascade radical cyclisations of methylenecyclopropane derivatives—syntheses of paeonilactone B and 6-epi-paeonilactone A
R. J. Boffey (2001)
10.1021/ja906396u
Studies on the mechanism, selectivity, and synthetic utility of lactone reduction using SmI(2) and H(2)O.
Dixit Parmar (2009)
10.1021/ja202103e
Scalable synthesis of cortistatin A and related structures.
Jun Shi (2011)
10.1021/ol100938j
Catalytic enantioselective total syntheses of bakkenolides I, J, and S: application of a carbene-catalyzed desymmetrization.
E. M. Phillips (2010)
10.1021/JA00121A037
Total Synthesis of (.+-.)-FR-900482
J. Schkeryantz (1995)
10.1002/CHEM.200401163
Photoinduced electron transfer reactions by SmI2 in THF: luminescence quenching studies and mechanistic investigations.
E. Prasad (2005)
10.1016/S0040-4020(01)89375-3
Catalytic asymmetric reductive amination of ketones via highly enantioselective hydrogenation of the CN double bond
M. Burk (1994)
10.1039/c1cc14252f
Selective reductive transformations using samarium diiodide-water.
M. Szostak (2012)
10.1039/A809277J
Is samarium diiodide an inner- or outer-sphere electron donating agent?
R. J. Enemærke (1999)
10.1039/b915662c
Stereospecific and highly stereoselective cyclopropanation reactions promoted by samarium.
José M. Concellón (2010)



This paper is referenced by
10.1021/ol502775w
Switching between reaction pathways by an alcohol cosolvent effect: SmI2-ethylene glycol vs SmI2-H2O mediated synthesis of uracils.
M. Szostak (2014)
10.1021/ol403668e
Electron transfer reduction of nitriles using SmI2-Et3N-H2O: synthetic utility and mechanism.
M. Szostak (2014)
10.1016/J.TET.2016.03.056
Highly selective SmI2–H2O-promoted radical cyclisation of five-membered lactones
Xavier Just-Baringo (2016)
10.1002/anie.201408324
Synthesis of polycyclic tertiary carbinamines by samarium diiodide mediated cyclizations of indolyl sulfinyl imines.
C. N. Rao (2015)
10.1039/c7ob00739f
Selective construction of quaternary stereocentres in radical cyclisation cascades triggered by electron-transfer reduction of amide-type carbonyls.
Huan-Ming Huang (2017)
10.1080/00397911.2018.1429634
Samarium(II) dibromide-promoted selective deprotection of a benzoyl protective group
Y. Yokoyama (2018)
10.1002/anie.201704086
Total Synthesis of (±)-Corymine.
Benxiang Zhang (2017)
10.1039/c3cc48932a
Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides.
M. Szostak (2014)
10.1039/c5cp02891d
Intriguing multichannel photoinduced electron transfer in lanthanide(iii)-diphenylamine systems.
P. Verma (2015)
10.3390/molecules22112018
Synthesis of Nitrogen Heterocycles Using Samarium(II) Iodide
Shicheng Shi (2017)
10.1021/jo501797w
Allylsamarium Bromide-Mediated Cascade Cyclization of Homoallylic Esters. Synthesis of 2-(2-Hydroxyalkyl)cyclopropanols and 2-(2-Hydroxyethyl)bicyclo[2.1.1]hexan-1-ols.
Mengmeng Shen (2015)
10.1021/ACSCATAL.7B00265
Acridinium Betaine as a Single-Electron-Transfer Catalyst: Design and Application to Dimerization of Oxindoles
D. Uraguchi (2017)
10.1002/anie.201708354
Radical Heterocyclization and Heterocyclization Cascades Triggered by Electron Transfer to Amide-Type Carbonyl Compounds.
Huan-Ming Huang (2017)
10.1021/jo5018525
Mechanism of SmI2/amine/H2O-promoted chemoselective reductions of carboxylic acid derivatives (esters, acids, and amides) to alcohols.
M. Szostak (2014)
10.1002/anie.201913645
Fragment coupling reactions in total synthesis that form carbon-carbon bonds via carbanionic or free radical intermediates.
Martin Tomanik (2019)
10.1002/anie.201505378
Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)-Substituted Bispyridinylidene
Samuel S. Hanson (2015)
10.1021/acs.joc.5b01572
A [2 + 3] Reductive Cyclodimerization of Quinoline by SmI2.
Ramesh Yella (2015)
10.1002/CHIN.201405252
Recent Advances in the Chemoselective Reduction of Functional Groups Mediated by Samarium(II) Iodide: A Single Electron Transfer Approach
M. Szostak (2014)
10.1016/J.TET.2015.06.007
Pinacol couplings of a series of aldehydes and ketones with SmI 2 /Sm/Me 3 SiCl in DME
A. Yoshimura (2015)
10.1002/EJOC.201800794
Selective Electron Transfer Reduction of Urea‐Type Carbonyls
Huan-Ming Huang (2019)
10.1021/acs.joc.7b00278
Reductive Bis-addition of Aromatic Aldehydes to α,β-Unsaturated Esters via the Use of Sm/Cu(I) in Air: A Route to the Construction of Furofuran Lignans.
Y. Liu (2017)
10.1021/ol500841b
A Sm(II)-mediated cascade approach to dibenzoindolo[3,2-b]carbazoles: synthesis and evaluation.
Matthew Levick (2014)
10.1039/c8ob01751d
Reduction of aromatic nitriles into aldehydes using calcium hypophosphite and a nickel precursor.
Rim Mouselmani (2018)
10.1002/SLCT.201700214
Pushing SmI2 Reactions towards the Limit‐ Entropy Driven Reduction of a Benzene Ring
S. Maity (2017)
10.1002/asia.201601712
Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal.
Y. Liu (2017)
10.1016/J.JALLCOM.2018.05.144
Synthesis and photophysical properties of crystalline [EuW10O36]9--based polyoxometalates with lanthanide ions as counter cations
Shumei Liu (2018)
10.1002/anie.201402891
Direct umpolung of glycals and related 2,3-unsaturated N-acetylneuraminic acid derivatives using samarium diiodide.
T. Le (2014)
10.1021/jacs.6b12077
Dearomatizing Radical Cyclizations and Cyclization Cascades Triggered by Electron-Transfer Reduction of Amide-Type Carbonyls.
Huan-Ming Huang (2017)
10.1021/ol502404e
Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using SmI2 and D2O as deuterium source under SET conditions.
M. Szostak (2014)
10.1002/9781118940228.CH1
Principles for Synthetic Efficiency and Expansion of the Field
Pei‐Qiang Huang (2018)
10.1021/jo4028243
Determination of the effective redox potentials of SmI₂, SmBr₂, SmCl₂, and their complexes with water by reduction of aromatic hydrocarbons. Reduction of anthracene and stilbene by samarium(II) iodide-water complex.
M. Szostak (2014)
10.1002/chem.201602717
Highly Chemoselective Synthesis of Indolizidine Lactams by SmI2 -Induced Umpolung of the Amide Bond via Aminoketyl Radicals: Efficient Entry to Alkaloid Scaffolds.
Shicheng Shi (2016)
See more
Semantic Scholar Logo Some data provided by SemanticScholar