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The [1, 3] O-to-C Rearrangement: Opportunities For Stereoselective Synthesis.

C. G. Nasveschuk, T. Rovis
Published 2008 · Chemistry, Medicine

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The relay of stereochemistry of a breaking C-O bond into a forming C-C bond is well-known in the context of [3, 3] sigmatropic shifts; however, this useful strategy is less well-known in other types of molecular rearrangements. Though the first successful example of a [1, 3] O-to-C rearrangement was reported more than 100 years ago, this class of reactions has received less attention than its [3, 3] counterpart. This perspective analyzes the various methods used for the activation and [1, 3] rearrangement of vinyl ethers with an emphasis on mechanism and applications to stereoselective synthesis. We also highlight our own contributions to this area.
This paper references
10.1016/S0040-4039(00)79600-6
Reaction of 2,3-unsaturated aryl glycosides with lewis acids : a convenient entry to C-aryl glycosides
N. G. Ramesh (1992)
10.1021/ja00415a024
Palladium-catalyzed 1,3-oxygen-to-carbon alkyl shifts. Basic studies
B. Trost (1981)
10.1016/S0040-4039(00)82404-1
Palladium(II) promoted carbocyclisation of aminodeoxyhex-5-enopyranosides
S. Adam (1988)
10.1021/JO026582F
Sulfur ylide-initiated thio-claisen rearrangements. The synthesis of highly substituted indolines.
A. Novikov (2003)
10.1002/JLAC.19214240205
Über die Isomerie der Formylphenylessigester. Alkylierung des Formylphenylessigesters
Wilhelm Wislicenus (1921)
10.1039/B316858A
Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols
Marianne F. Buffet (2004)
10.1039/P19790001455
Unsaturated carbohydrates. Part 21. A carbocyclic ring closure of a hex-5-enopyranoside derivative
R. Ferrier (1979)
10.1021/JA0105055
Total synthesis of (+)-phorboxazole A.
A. Smith (2001)
10.1021/JA00128A044
New Stereocontrolled Synthesis of Substituted Tetrahydrofurans from 1,3-Dioxolan-4-ones
N. A. Petasis (1995)
10.1016/S0040-4039(01)93337-4
Synthetic study toward vineomycins. Synthesis of c-aryl glycoside sector via Cp2HfCl2AgClO4-promoted tactics
T. Matsumoto (1989)
10.1021/AR00138A001
Chemistry and synthetic utility of cobalt-complexed propargyl cations
K. Nicholas (1987)
10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H
The total synthesis of the annonaceous acetogenin, muricatetrocin C.
D. Dixon (2002)
10.1021/ja00415a025
Palladium-catalyzed 1,3-oxygen-to-carbon alkyl shifts. A cyclopentanone synthesis
B. Trost (1981)
10.1246/CL.1981.1435
1,3-O- TO C-ALKYL MIGRATION OF 1-ALKENYL ALKYL ACETALS CATALYZED BY BORON TRIFLUORIDE. A NOVEL CROSS ALDOL TYPE REACTION
TakahashiMitsuru (1981)
10.1021/AR50155A001
New rules of selectivity: allylic alkylations catalyzed by palladium
B. Trost (1980)
10.1021/JA00542A059
Control of remote relative chiralities: a stereospecific total synthesis of dl-widdrol
S. Danishefsky (1980)
10.1016/S0040-4020(01)97594-5
Synthetic methods for the preparation of basic D- and L-pseudo-sugars. Synthesis of carbocyclic analogues of N-acetyl-muramyl-L-alanyl-D-isoglutamine (MDP)
D. H. Barton (1990)
10.1021/JO00389A600
Stereocontrolled Route to 2,3,5-Trisubstituted Tetrohydrofurans. Intermediates for the Total Synthesis of Polyether Antibiotics
H. Frauenrath (1987)
10.1021/JO00283A035
Spiro-fused 2,5-cyclohexadienones from the thermal 1,3-alkyl migrations of quinol vinyl ethers. A strategy for conversion of a carbonyl carbon to a quaternary carbon
S. Wang (1989)
10.1080/07328309208016150
Stereochemistry of the Palladium(II) Promoted Carbocyclization of Hex-5-Enopyranosides
P. László (1992)
10.1039/A706415B
Asymmetric Claisen rearrangement
H. Ito (1999)
10.1039/P19850002413
Unsaturated carbohydrates. Part 28. Observations on the conversion of 6-deoxyhex-5-enopyranosyl compounds into 2-deoxyinosose derivatives
R. Blattner (1985)
10.1021/JA060369+
Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy.
A. Smith (2006)
10.1021/JA00707A023
Stereochemistry of free-radical recombination reactions. Cage effect in decomposition of SS-(-)-azobis-.alpha.-phenylethane
F. D. Greene (1970)
10.1021/JA01610A023
1,3-Shifts. II. The Stereochemistry of the Rearrangement of α-Alkoxystyrenes1
K. Wiberg (1955)
10.1021/JA00761A073
Antarafacial allylic participation in a thermal 1,3-sigmatropic carbon migration
J. Baldwin (1972)
10.1039/C39910001699
[1.3], [3.3] and Tandem [1.3]–[3.3] rearrangements of 11- and 12-membered trienolides
K. Khan (1991)
10.1021/JO00232A024
Substituent effects in the aliphatic Claisen rearrangement of substituted (1-methyl-3-oxahexa-1,5-dienyl)amines: synthesis of substituted 2-aminopent-4-enals. Alternative [1,3[-sigmatropic shifts in related aromatic systems
J. Barluenga (1987)
10.1021/JA00954A025
Studies of Contact and Solvent-Separated Ion Pairs of Carbanions. II. Conductivities and Thermodynamics of Dissociation of Fluorenyllithium, -sodium, and -cesium
T. Hogen-Esch (1966)
10.1002/CBER.189602903102
Ueber eine eigenthümliche Umlagerung
L. Claisen (1896)
10.1021/JA00887A018
1,3-Shifts. VI. The Kinetics of the Rearrangement of α-Benzyloxystyrene
K. Wiberg (1963)
10.1016/0040-4039(96)00646-6
Silyl triflate-catalyzed oxonium-ene reaction of lactol allylic ethers: A new and stereocontrolled route to substituted oxygen heterocycles
K. Mikami (1996)
10.1007/s007060170056
Domino Reactions with 2-Fluoro-3-trifluoromethylfurans and -thiophenes [1]
K. Burger (2001)
10.1002/ANIE.199300831
A Diastereoselective Synthesis of β‐(N‐Acylamino)aldehydes by Rearrangement of O‐Vinyl‐N,O‐Acetals
H. Frauenrath (1993)
10.1039/A909300A
Oxygen to carbon rearrangements of anomerically linked alkenols from tetrahydropyran derivatives: an investigation of the reaction mechanism via a double isotopic labelling crossover study
Marianne F. Buffet (2000)
10.1351/pac199466102175
Total synthesis of aryl C-glycoside antibiotics
K. Suzuki (1994)
10.1016/J.TETLET.2003.10.119
Investigation of the Montmorillonite clay-catalyzed [1,3] shift reaction of 3-methyl-2-butenyl phenyl ether
Matthew R. Dintzner (2004)
10.1021/ja00528a055
A 1,3-O- to -C-alkyl shift catalyzed by palladium
B. Trost (1980)
10.1021/JO00244A004
Acyclic stereoselection for 1,2-diol systems via vinyl acetal rearrangement: control of relative stereochemistry in the rearrangement of 2,2,4-trimethyl-1,3-dioxolan-4-yl prop-1-enyl ethers to 2,3-dimethyl-3,4-(isopropylidenedioxy)butanals
H. Frauenrath (1988)
10.1021/JA982890C
Enantioselective Construction of Quaternary Stereocenters: Rearrangements of O-Acylated Azlactones Catalyzed by a Planar-Chiral Derivative of 4-(Pyrrolidino)pyridine
J. C. R. and (1998)
10.1021/JA0744448
An expedient formal total synthesis of (-)-diazonamide A via a powerful, stereoselective O-aryl to C-aryl migration to form the C10 quaternary center.
C. Cheung (2007)
10.1055/S-1998-1866
Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of lactols.
Marianne F. Buffet (1998)
10.1021/JA00157A049
Organoaluminum-promoted Claisen rearrangement of allyl vinyl ethers
K. Nonoshita (1990)
10.1021/JO0517895
Development of the scope of a co-mediated O-->C rearrangement reaction.
Simon J Meek (2005)
10.1016/S0040-4039(00)89033-4
Clay catalyzed rearrangement of substituted allyl phenyl ethers: Synthesis of ortho-allyl phenols, chromans and coumarans
W. G. Dauben (1990)
10.1021/OL0500620
Investigations into the role of ion pairing in reactions of heteroatom-substituted cyclic oxocarbenium ions.
Siddhartha R Shenoy (2005)
10.1021/JO0300587
Investigation of a stereoselective co-mediated rearrangement reaction.
D. R. Carbery (2003)
10.1021/JA01081A059
Solvent-Separated Ion Pairs of Carbanions
T. Hogen-esch (1965)
10.1021/OL061380H
Efficient N-heterocyclic carbene-catalyzed O- to C-acyl transfer.
Jennifer E. Thomson (2006)
10.1016/S0040-4039(00)97693-7
Improvement in O→C-glycoside rearrangement approach to C-aryl glycosides: Use of 1-O-acetyl sugar as stable but efficient glycosyl donor
T. Matsumoto (1990)
10.1021/AR50060A003
Orbital-symmetry-forbidden reactions
J. Berson (1972)
10.1055/S-1989-27408
Ein newer allgemeiner Zugang zu α-trifluormethyl-substituierten aromatischen und heteroaromatischen α-Aminosäuren
K. Burger (1989)
10.1016/J.TET.2006.02.042
Surveying approaches to the formation of carbon-carbon bonds between a pyran and an adjacent ring.
Jeffrey D. Frein (2006)
10.1016/S0040-4039(03)00610-5
1,3-Rearrangement of ketene-N,O-acetals
T. Suzuki (2003)
10.1021/OL048418F
Spongistatin synthetic studies. evolution of a scalable synthesis for the EF fragment of (+)-Spongistatin 1 exploiting a Petasis-Ferrier union/rearrangement tactic.
A. Smith (2004)
10.1021/JA037935A
Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.
Leticia Ayala (2003)
10.1002/(SICI)1521-3773(20000117)39:2<362::AID-ANIE362>3.0.CO;2-1
Carbocyclic Ring Closure of Unsaturated S-, Se-, and C-Aryl Glycosides.
Matthieu Sollogoub (2000)
10.1016/0040-4020(77)80284-6
Organopalladium intermediates in organic synthesis
B. Trost (1977)
10.1002/1615-4169(200209)344:8<845::AID-ADSC845>3.0.CO;2-5
Catalyzed Reactions of Enolates and Cations: A Novel Method for Enolate Alkylation
A. Gansäuer (2002)
10.1055/S-1993-22609
Diastereodivergent Formation of 2,3-trans:3,4-cis- and 2,3-cis:3,4-trans-2,3,4-Trisubstituted Tetrahydrofurans from the Common 2,5-Disubstituted-4,5-dihydro-1,3-dioxepin: A Diastereocontrolled Route to Furofuran Lignan (±)-Asarinin
Seiichi Takano (1993)
10.1021/JA037223K
Development of chiral nucleophilic pyridine catalysts: applications in asymmetric quaternary carbon synthesis.
Scott A. Shaw (2003)
10.1021/OL062042J
Regio- and stereoselective Ferrier reaction of O-1,3-dienyl acetals promoted by organoaluminum complexes.
E. Tayama (2006)
10.1021/JA01448A031
A COMPARISON OF THE ACTIVITY OF CERTAIN UNSATURATED GROUPS WITH THE ACTIVITY OF THE ALLYL GROUP IN CERTAIN ETHERS.1
S. G. Powell (1920)
10.1021/JA00751A038
Claisen rearrangement of 2-methyl-2-vinyl-5-methylenetetrahydrofuran
S. Rhoads (1971)
10.1039/B605438B
A modular approach to the synthesis of 2,3,4-trisubstituted tetrahydrofurans.
C. G. Nasveschuk (2006)
10.1021/OL990830L
Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement.
A. Smith (1999)
10.1021/OL990829M
Phorboxazole synthetic studies. 2. Construction of a C(20-28) subtarget, a further extension of the Petasis-Ferrier rearrangement.
A. Smith (1999)
10.1002/ANIE.199704931
Novel Carbocyclic Ring Closure of Hex‐5‐enopyranosides
S. Das (1997)
10.1002/ADSC.200303059
Catalyzed Reactions of Enol Ethers with SN1 Active Groups: A Novel Method for the Preparation of α‐Alkylated Ketones
A. Gansäuer (2003)
10.1021/JA01569A046
1,3-Shifts. V. The Intermolecular Nature of Some 1,3-Shifts
K. Wiberg (1957)
10.1021/JA01339A033
The Molecular Rearrangement of Alpha,Beta-Unsaturated Ethers1
W. Lauer (1933)
10.1039/C29690000264
Synthesis of 2,2,5-trimethylcyclohept-4-enone (karahanaenone)via a new terpene cyclisation
E. Demole (1969)
10.1021/OL0505151
Regioselective Lewis acid-mediated [1,3] rearrangement of allylvinyl ethers.
C. G. Nasveschuk (2005)
10.1021/JA993366O
Stereochemical Reversal of Nucleophilic Substitution Reactions Depending upon Substituent: Reactions of Heteroatom-Substituted Six-Membered-Ring Oxocarbenium Ions through Pseudoaxial Conformers
J. Romero (2000)
10.1016/0040-4039(95)02114-0
Stereocontrolled synthesis of substituted tetrahydropyrans from 1,3-dioxan-4-ones
N. A. Petasis (1996)
10.1002/(SICI)1099-0690(199909)1999:9<2103::AID-EJOC2103>3.0.CO;2-K
Direct Synthesis of Pseudo‐Disaccharides by Rearrangement of Unsaturated Disaccharides
Alan J. Pearce (1999)
10.1002/HLCA.19240070146
Insektentötende Stoffe VI. Untersuchungen über Cyclopentanolonderivate und ihr Vergleich mit dem Pyrethrolon
H. Staudinger (1924)
10.1055/S-1998-1867
DIASTEREOSELECTIVE ANOMERIC OXYGEN TO CARBON REARRANGEMENTS OF SILYL ENOL ETHER DERIVATIVES OF LACTOLS
D. Dixon (1998)
10.1016/S0040-4039(00)89379-X
Über eine einfache darstellung von acyl-oxazolinonen-(5) aus 5-acyloxy-oxazolen II. Mitteilung über hypernucleophile acylierungskatalysatoren
W. Steglich (1970)
10.1055/S-1989-27158
The hetero-cope rearrangement in organic synthesis
S. Blechert (1989)
10.1002/CHIN.198029140
Competitive [1,3]- and [3,3]-sigmatropic rearrangements
R. T. Arnold (1980)
10.1021/jo00133a011
Reactivity of 2-ethoxy-5-alkyl-3,4-dihydro-2H-pyrans toward aluminum alkyls: stereoselective preparation of cyclobutyl derivatives
R. Menicagli (1982)
10.1002/1521-3773(20020715)41:14<2584::AID-ANIE2584>3.0.CO;2-I
Development of a co-mediated rearrangement reaction.
D. R. Carbery (2002)
10.1016/S0040-4039(00)87026-4
1,3-O- to -C-alkyl migration of 1-alkenyl alkyl acetals and ketals catalyzed by boron trifluoride. Selective cross- and regioselective aldol type reactions
M. Takahashi (1982)
10.1021/JA056150X
Enantioselective TADMAP-catalyzed carboxyl migration reactions for the synthesis of stereogenic quaternary carbon.
Scott A. Shaw (2006)
10.1016/S0040-4039(00)74541-2
Reactivity of 2-ethoxy-5-alkyl-3,4-dihydro-2H-pyrans towards aluminum alkyls : a facile synthesis of cyclobutylmethanols
R. Menicagli (1980)
10.1021/JA00306A044
Tandem electrocyclic-sigmatropic reaction of benzocyclobutenes. An expedient route to 4,4-disubstituted isochromanones
K. Shishido (1985)
10.1021/JA00399A090
Stereo- and regiochemistry of a palladium-catalyzed oxygen to carbon migration
B. Trost (1981)
10.1055/S-1988-27788
Boron Trifluoride-Catalyzed Rearrangement of 2-Aryloxytetrahydropyrans: A New Entry to C-Arylglycosidation
T. Kometani (1988)
10.1016/S0040-4039(00)88688-8
Diastereoselection in 1,3-O- to -C-alkyl migration reaction of 1-alkenyl alkyl acetals catalyzed by boron trifluoride etherate
M. Takahashi (1982)
10.1002/ANIE.199104771
The Isoinversion Principle—a General Model of Chemical Selectivity
Helmut Buschmann (1991)
10.1021/JA051420X
Total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis synthetic strategy.
A. Smith (2005)
10.1002/CBER.19821150806
Carboxonium-Ionen-Reaktionen cyclischer Acetale, VI. Der sterische Verlauf der säurekatalysierten Umlagerung von 4,5-Dihydro-1,3-dioxepinen zu Tetrahydrofuran-3-carbaldehyden
H. Frauenrath (1982)
10.1021/JO00277A002
Synthesis of biologically active carbocyclic analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP)
D. H. Barton (1989)
10.1021/JA01872A037
The Condensation of α-Methoxystyrene with Hydrocarbons
M. Spielman (1939)
10.1021/OL062329G
Development of a stereoselective co-mediated dihydropyran ring contraction.
Simon J Meek (2006)
10.1021/jo00928a004
Stereochemistry and mechanism of the thermal [1,3] alkyl shift of stable 1,4-dialkyl-1,4-dihydropyrazines
J. Lown (1974)
10.1021/JA00954A024
Studies of Contact and Solvent-Separated Ion Pairs of Carbanions. I. Effect of Temperature, Counterion, and Solvent
T. E. H. Esch (1966)
10.1039/A806584E
A total synthesis of (+)-Goniodiol using an anomeric oxygen-to-carbon rearrangement
D. Dixon (1998)
10.1002/(SICI)1521-3757(19990315)111:6<819::AID-ANGE819>3.0.CO;2-S
NEUE FORTSCHRITTE BEI DER UMWANDLUNG VON KOHLENHYDRATFURANOSIDEN UND -PYRANOSIDEN ZU CARBOCYCLEN
P. Dalko (1999)
10.1021/JA01631A055
The Stereochemistry of Aromatic Alkylations. II. The Thermal Rearrangement of Alkyl Aryl Ethers1
H. Hart (1954)
10.1021/JO00247A015
New type of 1,3-molecular rearrangement of substituted-vinyl alkoxymethyl ethers and its application to synthesis of 1(or 3)-substituted 4-alkoxybutan-2-ones
X. Gu (1988)
10.1039/B001243M
Diastereoselective oxygen to carbon rearrangements of anomerically linked enol ethers and the total synthesis of (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a component of civet
D. Dixon (2000)
10.1002/ANIE.200500088
Stereoselective Lewis acid mediated [1,3] ring contraction of 2,5-dihydrooxepins as a route to polysubstituted cyclopentenes.
C. G. Nasveschuk (2005)
10.1021/JA00014A069
[1,3]-Sigmatropic rearrangement of allyl vinyl ethers at ambient temperature in 3.0 M lithium, perchlorate-diethyl ether
P. A. Grieco (1991)
10.1021/OL991238Z
Synthesis of the spirocyclic cyclohexadienone ring system of the schiarisanrins.
R. S. Coleman (2000)
10.1016/S0040-4039(00)88479-8
New approach to C-aryl glycosides starting from phenol and glycosyl fluoride. Lewis acid-catalyzed rearrangement of O-glycoside to C-glycoside
T. Matsumoto (1988)
10.1021/CR020703U
Claisen rearrangement over the past nine decades.
A. Castro (2004)
10.1021/JA01337A026
The Kinetics of the Rearrangement of α-Methoxystyrene1
F. H. Macdougall (1933)
10.1016/S0040-4039(02)01168-1
[1,3] Sigmatropic rearrangement of ketene silyl acetals derived from benzyl α-substituted propanoates
Isamu Shiina (2002)
10.1016/0040-4039(88)85184-0
Spirodienones via a thermal uncatalyzed [1,3]-oxygen-to-carbon migration
G. W. Morrow (1988)
10.1016/J.TET.2003.03.004
1,3-Polyol arrays via the stereoselective rearrangement of vinyl acetals
Y. Zhang (2003)
10.1021/CR00061A001
Catalysis of the Cope and Claisen rearrangements
R. Lutz (1984)
10.1039/C39840001427
Synthesis of substituted 2-aminopent-4-enals and 2-amino-3-(2-furyl)propanals via[3,3]- and [1,3]-sigmatropic shifts of β-allyloxyenamines
J. Barluenga (1984)
10.1021/JA026972J
Stereoretentive O-to-C rearrangement of vinyl acetals: solvent cage effects as a stereocontrol element.
Y. Zhang (2002)
10.1002/CBER.19120450348
Über Umlagerung von Phenol-allyläthern in C-Allyl-phenole
L. Claisen (1912)



This paper is referenced by
10.1002/jms.1915
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase.
M. S. Morales-Ríos (2011)
10.1021/ja906745j
Reactions of ruthenium Cp phosphine complex with 4,4-disubstituted-1,6-enynes: effect of methyl substituents in the olefinic fraction.
Chia-Pei Chung (2009)
10.1021/jo302152j
Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers: missing transition states revealed through evolution of aromaticity, Au(I) as an oxophilic Lewis acid, and lower energy barriers from a high energy complex.
Dinesh V. Vidhani (2013)
10.1021/acs.joc.5b01031
Cyclic α-Alkoxyphosphonium Salts from (2-(Diphenylphosphino)phenyl)methanol and Aldehydes and Their Application in Synthesis of Vinyl Ethers and Ketones via Wittig Olefination.
Wenhua Huang (2015)
10.1039/c6cc01016d
Synthesis of benzofurans via an acid catalysed transacetalisation/Fries-type O → C rearrangement/Michael addition/ring-opening aromatisation cascade of β-pyrones.
Siddheshwar K. Bankar (2016)
10.1039/C4SC00879K
Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies
Eoin R. Gould (2014)
10.1038/s41467-019-11245-2
Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement
B. Zhou (2019)
The influence of chemical structure of novel surfactants on the antibacterial activity and their interactions with DNA
Katarzyna Bury (2016)
10.1126/science.aau4821
Catalytic palladium-oxyallyl cycloaddition
B. Trost (2018)
10.1021/OM400742X
Tandem Cyclization of Enynes Containing a Thioether or Ether Linkage via Ruthenium Allenylidene and Vinylidene Complexes
Y. Feng (2013)
10.1016/J.TET.2017.10.055
A new synthesis of highly functionalized cyclohexenes via a vinylogous Ferrier-Petasis cyclization reaction
Anna Domżalska (2017)
10.1002/anie.201910710
Biomimetic Synthesis of Meroterpenoids by Dearomatization- Driven Polycyclization.
J. Porco (2019)
10.1002/chem.201801062
Catalytic [1,3] O-to-C Rearrangement: Rapid Access to Bridged Bicyclic Systems.
Jiantao Zhang (2018)
10.1021/ACS.ORGLETT.6B02459
Tandem O-H Insertion/[1,3]-Alkyl Shift of Rhodium Azavinyl Carbenoids with Benzylic Alcohols: A Route To Convert C-OH Bonds into C-C Bonds.
Pengbing Mi (2016)
10.1039/d0cc01017k
Stepwise approach for sterically hindered Csp3-Csp3 bond formation by dehydrogenative O-alkylation and Lewis acid-catalyzed [1,3]-rearrangement towards the arylalkylcyclopentane skeleton of sesquiterpenes.
Ban Fujitani (2020)
10.1016/j.jorganchem.2020.121651
Synthesis of pyrrole-ferrocene ensembles and their rearrangement into 2-(ferrocenylmethyl)-1,2-dihydro-3H-pyrrol-3-ones
Ol'ga A. Tarasova (2020)
10.1021/ol402237w
Preparation of α-imino aldehydes by [1,3]-rearrangements of O-alkenyl oximes.
Dimitra Kontokosta (2013)
10.1021/JACS.6B09727
Syntheses of (+)-30-epi-, (-)-6-epi-, (±)-6,30-epi-13,14-Didehydroxyisogarcinol and (±)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective, Lewis Acid-Controlled Cyclizations.
Jonathan H Boyce (2016)
10.1039/C9GC01030K
Synthesis of functionalized 3-isochromanones via metal-free intramolecular alkoxylation-initiated cascade cyclization
Yingqi Zhang (2019)
10.1002/ANIE.201302572
Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.
A. C. Jones (2014)
10.1021/jo200061b
Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes.
Heng-Yen Wang (2011)
10.1016/B978-0-08-097742-3.00624-8
6.16 Functional Group Transformation via Allyl Rearrangement
Z. Gu (2014)
10.1021/ja208156z
A dual-catalysis approach to the asymmetric Steglich rearrangement and catalytic enantioselective addition of O-acylated azlactones to isoquinolines.
C. K. De (2011)
10.1016/J.TET.2011.10.031
Palladium-Catalyzed Asymmetric Alkylation in the Synthesis of Cyclopentanoid and Cycloheptanoid Core Structures Bearing All-Carbon Quaternary Stereocenters.
Allen Y Hong (2011)
10.3762/bjoc.14.172
Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines
I. Nakamura (2018)
10.1039/b806492j
Brønsted acid catalyzed regioselective aza-Ferrier reaction: a novel synthetic method for alpha-(N-Boc-2-pyrrolidinyl) aldehydes.
E. Tayama (2008)
10.1021/acs.orglett.7b00389
K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes To Form Pyridols.
S. Wang (2017)
10.1039/C5QO00397K
Gold(I) catalyzed [1,3] O → C rearrangement of benzylvinyl ethers
Chandrababu Naidu Kona (2016)
10.1039/c3cc49629e
Gold(I)-catalysed [1,3] O→C rearrangement of allenyl ethers.
Chandrababu Naidu Kona (2014)
10.1039/c9sc00079h
Metal-free alkene carbooxygenation following tandem intramolecular alkoxylation/Claisen rearrangement: stereocontrolled access to bridged [4.2.1] lactones† †Electronic supplementary information (ESI) available. CCDC 1831051, 1831053, 1831054 and 1864037. For ESI and crystallographic data in CIF or o
L. Li (2019)
10.1002/anie.200803610
Catalytic asymmetric aminoallylation of aldehydes: a catalytic enantioselective aza-Cope rearrangement.
M. Rueping (2008)
10.1002/9780470066614.CH13
Molecular Rearrangements: Part 1. Pericyclic Molecular Rearrangements
S. Armstrong (2011)
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