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Ethylene In Organic Synthesis: A New Route To Anticholenergic Pyrrolidinoindolines, And Other Molecules With All Carbon-quaternary Centers Via Asymmetric Hydrovinylation.

Hwan Jung Lim, T. V. RajanBabu
Published 2011 · Chemistry, Medicine

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The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3,3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.
This paper references
10.1021/JA01306A046
Studies in the Indole Series. III. On the Synthesis of Physostigmine
P. L. Julian (1935)
10.1016/0040-4020(80)80024-X
Methodology for the construction of quaternary carbon centers
S. Martin (1980)
10.1248/CPB.30.2641
Enantioselective synthesis of (-)-physostigmine.
S. Takano (1982)
10.3987/COM-87-4414
Practical synthesis of unnatural (+)-physostigmine and carbamate analogues
A. Brossi (1988)
10.1039/C39890001591
Enantiocontrolled synthesis of (+)-aphanorphine from (R)-O-benzylglycidol: assignment of absolute configuration
S. Takano (1989)
10.1021/JO00002A074
Asymmetric alkylation of oxindoles: an approach to the total synthesis of (-)-physostigmine
T. C. Lee (1991)
10.3987/COM-91-5814
A total synthesis of (−)-physostigmine
M. Node (1991)
10.1016/S0040-4020(01)91024-5
Chiral non-racemic bicyclic lactams. Vehicles for the construction of natural and unnatural products containing quaternary carbon centers.
D. Romo (1991)
10.1021/JM00092A011
Benzazepinone calcium channel blockers. 5. Effects on antihypertensive activity associated with N1 and aromatic substituents.
J. Das (1992)
10.1007/978-1-4612-2908-7
Alkaloids: Chemical and Biological Perspectives
S. Pelletier (1992)
10.1021/JA00040A013
The enantioselective synthesis of (-)-physostigmine via chiral sulfoxides
J. Marino (1992)
10.1021/JA00103A600
Catalytic asymmetric synthesis of benzylic quaternary carbon centers. An efficient synthesis of (-)-eptazocine
T. Takemoto (1993)
10.1002/MED.2610150103
Phenserine and ring C hetero‐analogues: Drug candidates for the treatment of Alzheimer's disease
N. Greig (1995)
10.1021/JO00110A033
Asymmetric Synthesis of the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine
A. Hulme (1995)
10.1002/9783527618231
Applied Homogeneous Catalysis with Organometallic Compounds
B. Cornils (1996)
10.3987/COM-96-7421
Asymmetric Synthesis of Benzylic Quaternary Carbon Center via an Enzymatic Reaction
S. Shiotani (1996)
10.1016/S0957-4166(96)00538-1
Enzymatic asymmetrisation of prochiral α,α-disubstituted-malonates and -1,3-propanediols: formal asymmetric syntheses of (−)-aphanorphine and (+)-eptazocine
A. Fadel (1997)
10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO;2-V
The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters.
E. Corey (1998)
10.1021/JA980788+
Catalytic Asymmetric Synthesis of Either Enantiomer of the Calabar Alkaloids Physostigmine and Physovenine
A. Matsuura (1998)
10.1021/OL005513P
An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization.
M. Kawahara (2000)
10.1021/OL006065O
An expedient route to the Calabar bean alkaloids (-)-physovenine and (-)-physostigmine.
A. El-Azab (2000)
10.1021/JO005761Z
Improved catalysts for the palladium-catalyzed synthesis of oxindoles by amide alpha-arylation. Rate acceleration, use of aryl chloride substrates, and a new carbene ligand for asymmetric transformations.
S. Lee (2001)
10.1039/b208045a
Oxazolines as chiral building blocks for imidazolium salts and N-heterocyclic carbene ligands.
F. Glorius (2002)
10.1021/JA012099V
Highly enantioselective nickel-catalyzed hydrovinylation with chiral phosphoramidite ligands.
G. Franciò (2002)
10.1021/JO026438U
Application of vicarious nucleophilic substitution to the total synthesis of dl-physostigmine.
Pankaj D. Rege (2003)
10.1016/S0957-4166(03)00117-4
An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine
S. Taylor (2003)
10.1021/CR020040G
Asymmetric hydrovinylation reaction.
T. V. RajanBabu (2003)
10.1002/ANIE.200351666
Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter.
Ivory D. Hills (2003)
10.1016/J.TET.2003.10.039
Stereoselective formation of quaternary carbon centers and related functions
I. Denissova (2003)
10.1021/JA046690E
Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine.
Audris Huang (2004)
10.1021/JA0478779
Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents. An effective method for enantioselective synthesis of tertiary and quaternary carbons.
M. Kacprzynski (2004)
10.1073/PNAS.0307113101
Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.
C. Douglas (2004)
10.1002/3527606858
Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis
J. Christoffers (2005)
10.1021/JO051550O
Dichloroketene-induced cyclizations of vinyl sulfilimines: application of the method in the synthesis of (+/-)-desoxyeseroline.
A. Padwa (2005)
10.1016/J.TET.2005.07.030
A formal synthesis of (′)-physostigmine via 3,3-rearrangement of a bis-enamine
P. F. Santos (2005)
10.1021/JA054447P
Total synthesis of (+/-)-taiwaniaquinol B via a domino intramolecular friedel-crafts acylation/carbonyl alpha-tert-alkylation reaction.
E. Fillion (2005)
10.1021/JA060999B
All-Carbon Quaternary Centers via Catalytic Asymmetric Hydrovinylation. New Approaches to the Exocyclic Side Chain Stereochemistry Problem
Aibin Zhang (2006)
10.1021/JA062505G
Synthesis of taiwaniaquinoids via Nazarov triflation.
Guangxin Liang (2006)
10.1021/JA060560J
Molybdenum-catalyzed asymmetric allylation of 3-alkyloxindoles: application to the formal total synthesis of (-)-physostigmine.
B. Trost (2006)
10.1039/B505080D
Azide rearrangements in electron-deficient systems.
S. Lang (2006)
10.1021/JA061853F
The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone.
Ryan M. L. McFadden (2006)
10.1016/J.TETLET.2005.12.098
Development of an N-heterocyclic carbene ligand based on concept of chiral mimetic
T. Arao (2006)
10.1021/JA057654Y
Highly enantioselective hydrovinylation of alpha-alkyl vinylarenes. an approach to the construction of all-carbon quaternary stereocenters.
W. Shi (2006)
10.1039/B614999E
Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine.
John F Bower (2007)
10.1002/ANIE.200703408
Bulky chiral carbene ligands and their application in the palladium-catalyzed asymmetric intramolecular alpha-arylation of amides.
E. P. Kuendig (2007)
10.1021/JA068723R
Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes.
B. Corkey (2007)
10.1002/ANIE.200701055
Formal synthesis of (-)-aphanorphine using sequential photomediated radical reactions of dithiocarbamates.
R. Grainger (2007)
10.1021/JA067289Q
Organocatalytic Asymmetric Direct a-Alkynylation of Cyclic -Ketoesters.
T. B. Poulsen (2007)
10.1002/ANIE.200700612
Total synthesis of complex cyclotryptamine alkaloids: stereocontrolled construction of quaternary carbon stereocenters.
A. Steven (2007)
10.1021/ja805088r
Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2Cl.
Yoshiaki Nakao (2008)
10.15227/ORGSYN.085.0248
(R)-3-METHYL-3-PHENYL-1-PENTENE VIA CATALYTIC ASYMMETRIC HYDROVINYLATION.
C. Smith (2008)
10.1021/ol801168j
Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation.
Y. Yasui (2008)
10.1021/ol800737d
Enantiocontrolled synthesis of (-)-9-epi-pentazocine and (-)-aphanorphine.
X. Yang (2008)
10.1021/ja901018g
IBiox[(-)-menthyl]: a sterically demanding chiral NHC ligand.
Sebastian Wuertz (2009)
10.1002/anie.200802938
Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.
J. Bower (2009)
10.1002/anie.200902943
Catalytic enantioselective stereoablative alkylation of 3-halooxindoles: facile access to oxindoles with C3 all-carbon quaternary stereocenters.
Sandy Ma (2009)
10.1002/anie.200901277
Phosphonium salts as chiral phase-transfer catalysts: asymmetric Michael and Mannich reactions of 3-aryloxindoles.
R. He (2009)
10.1016/J.TETLET.2009.03.012
A novel and efficient total synthesis of (±)-physostigmine
M. G. Kulkarni (2009)
10.1021/ja903520c
Thiourea-catalyzed highly enantio- and diastereoselective additions of oxindoles to nitroolefins: application to the formal synthesis of (+)-physostigmine.
T. Bui (2009)
10.1021/ja903880q
Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.
Alexander M. Taylor (2009)
10.1021/ja805541u
AcOLeDMAP and BnOLeDMAP: conformationally restricted nucleophilic catalysts for enantioselective rearrangement of indolyl acetates and carbonates.
T. A. Duffey (2009)
10.1055/S-0028-1088213
In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.
T. V. RajanBabu (2009)
10.1021/jo901972b
Efficient asymmetric synthesis of abeo-abietane-type diterpenoids by using the intramolecular Heck reaction.
M. Node (2010)
10.1021/ol1003093
Highly chemo- and enantioselective synthesis of 3-allyl-3-aryl oxindoles via the direct palladium-catalyzed alpha-arylation of amides.
X. Luan (2010)
10.1021/ja107328g
Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.
Lindsay M. Repka (2010)
10.1021/jo100769n
Organocatalytic enantioselective hydroxymethylation of oxindoles with paraformaldehyde as C1 unit.
Xiong-Li Liu (2010)
10.1021/np9004695
The taiwaniaquinoids: a review.
G. Majetich (2010)
10.1021/ja103428y
Cyclopropylazetoindolines as precursors to C(3)-quaternary-substituted indolines.
Vinson R. Espejo (2010)
10.1039/c0cc05222a
Enantioselective synthesis of all-carbon quaternary stereogenic centers in acyclic systems.
Jaya Prakash Das (2011)
10.1021/ja110215b
Enantioselective total syntheses of (-)-taiwaniaquinone H and (-)-taiwaniaquinol B by iridium-catalyzed borylation and palladium-catalyzed asymmetric α-arylation.
Xuebin Liao (2011)
10.1021/ja2039248
Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling.
Ping Zhang (2011)
10.1002/EJOC.201100091
Concise Route to (–)‐ and (+)‐Aphanorphine
M. Medjahdi (2011)
10.1021/ol2009895
Enantioconvergent synthesis of (+)-aphanorphine via asymmetric Pd-catalyzed alkene carboamination.
D. N. Mai (2011)



This paper is referenced by
10.1002/ajoc.202000193
Synthetic Applications of Cyclopropene and Cyclopropenone: Recent Progress and Developments
Bishnu Prasad Raiguru (2020)
10.1021/acs.orglett.9b03382
Highly Enantioselective Iridium-Catalyzed Cascade Double Allylation Strategy: Synthesis of Pyrrolidinoindolines with an All-Carbon Quaternary Stereocenter.
Hua Tian (2019)
10.1021/acs.orglett.7b01651
Visible-Light-Mediated Addition of Phenacyl Bromides onto Cyclopropenes.
Nitin S Dange (2017)
10.1021/acs.orglett.7b03188
Retraction of "An Expeditious Route to Both Enantiomers of All Carbon Quaternary Stereocenters at C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement: Total Synthesis of (-)-Physostigmine".
G. Pandey (2017)
10.1002/chem.201504010
tert-Butyl Iodide Mediated Reductive Fischer Indolization of Conjugated Hydrazones.
Y. Ito (2016)
10.1021/acs.joc.6b01049
A Synthetic Route to Chiral Tetrahydropyrroloindoles via Ring Opening of Activated Aziridines with 2-Bromoindoles Followed by Copper-Catalyzed C-N Cyclization.
M. Sayyad (2016)
10.1016/J.TET.2016.01.039
Construction of 3-amino-2-oxindoles by direct amination of aniline or α-amino-acid derivatives to 3-bromooxindoles
M. Zhao (2016)
10.1016/J.TET.2015.01.049
A metal-free synthesis of oxindoles by a radical addition-cyclization onto N-arylacrylamides with xanthates
S. Wang (2015)
10.1021/acs.orglett.5b03082
Unified Approach to the Spiro(pyrrolidinyl-oxindole) and Hexahydropyrrolo[2,3-b]indole Alkaloids: Total Syntheses of Pseudophrynamines 270 and 272A.
Subhadip De (2015)
10.1039/C5QO00091B
Pd-catalyzed Heck cyclization and in situ hydrocarboxylation or hydromethenylation via a hydrogen borrowing strategy
Xianglei Liu (2015)
10.1021/acs.joc.5b01768
Domino Michael-Michael and Aldol-Aldol Reactions: Diastereoselective Synthesis of Functionalized Cyclohexanone Derivatives Containing Quaternary Carbon Center.
M. K. Ghorai (2015)
10.1016/B978-0-08-097742-3.00533-4
5.32 Hydrovinylation Reactions in Organic Synthesis
T. V. RajanBabu (2014)
10.1002/chem.201304982
Carbamoyl Radical-Mediated Synthesis and Semipinacol Rearrangement of β-Lactam Diols
M. Betou (2014)
10.1002/ADSC.201300864
Highly Efficient Catalytic Dimerization of Styrenes via Cationic Palladium(II) Complexes
J. H. Choi (2013)
10.1002/anie.201303916
Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.
Vaneet Saini (2013)
10.1002/9783527652235.CH37
Asymmetric Hydrovinylation of Alkenes
T. V. RajanBabu (2013)
10.1002/ANGE.201303916
Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab
Vaneet Saini (2013)
10.1039/C3CY00084B
Metal catalysed hydrovinylation
R.Ma. Ceder (2013)
10.1039/c3cc43257b
Domino Rh-catalyzed hydroformylation-double cyclization of o-amino cinnamyl derivatives: applications to the formal total syntheses of physostigmine and physovenine.
Wen-Hua Chiou (2013)
10.1021/jo4017953
Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.
Lindsay M. Repka (2013)
10.1021/ol302388t
Enantioselective cyclopropanation of indoles: construction of all-carbon quaternary stereocenters.
Guelsuem Oezueduru (2012)
10.1016/B978-0-08-095167-6.00518-8
5.16 Reduction: Enantioselective Hydrovinylation of Alkenes
T. V. RajanBabu (2012)
10.1021/ja3004733
Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B.
W. Liu (2012)
10.1002/anie.201203553
Enantioselective construction of pyrroloindolines catalyzed by chiral phosphoric acids: total synthesis of (-)-debromoflustramine B.
Z. Zhang (2012)
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