Ligand effects in the organolithium-mediated enantioselective alpha-deprotonation of achiral epoxides

Ligand effects in the organolithium-mediated enantioselective alpha-deprotonation of achiral epoxides

The enantioselective α-deprotonation-rearrangement of achiral epoxides using organolithiums with C2-symmetric ligands [bisoxazolines 4a-d and (-)-α-isosparteine 5] is described.

Bibliografiske detaljer
Main Authors:	Hodgson, D, Lee, G
Format:	Journal article
Sprog:	English
Udgivet:	1997

Lignende værker

Enantioselective synthesis of epoxides by alpha-deprotonation--electrophile trapping of achiral epoxides.
af: Hodgson, D, et al.
Udgivet: (2003)

Isomerisations of cycloalkene- and bicycloalkene-derived achiral epoxides by enantioselective alpha-deprotonation
af: Hodgson, D, et al.
Udgivet: (1998)

Enantioselective alpha-deprotonation of epoxides.
af: Hodgson, D
Udgivet: (2001)

Enantioselective alpha-deprotonation-rearrangement of meso-epoxides
af: Hodgson, D, et al.
Udgivet: (1996)

Enantioselective desymmetrisation of achiral epoxides
af: Hodgson, D, et al.
Udgivet: (1996)

Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides
af: Hodgson, D, et al.
Udgivet: (2001)

Synthesis of (-)-xialenon A by enantioselective alpha-deprotonation-rearrangement of a meso-epoxide
af: Hodgson, D, et al.
Udgivet: (2003)

A new and enantioselective indolizidine synthesis by meso-epoxide alpha-deprotonation-transannular N-C insertion
af: Hodgson, D, et al.
Udgivet: (1999)

Chiral epoxides by desymmetrizing deprotonation of meso-epoxides.
af: Hodgson, D, et al.
Udgivet: (2002)

Organolithium-induced enantioselective alkylative double ring-opening of epoxides: synthesis of enantioenriched unsaturated amino alcohols
af: Hodgson, D, et al.
Udgivet: (2004)

First direct deprotonation-electrophile trapping of simple epoxides: synthesis of alpha,beta-epoxysilanes from terminal epoxides.
af: Hodgson, D, et al.
Udgivet: (2001)

Deprotonation-electrophile trapping of terminal epoxides.
af: Hodgson, D, et al.
Udgivet: (2005)

Enantioselective rearrangements of bicyclo[2.2.1]- and bicyclo[2.2.2]alkene-derived achiral epoxides to ketones
af: Hodgson, D, et al.
Udgivet: (1997)

Unsaturated 1,2-amino alcohols from dihydropyrrole epoxides and organolithiums
af: Hodgson, D, et al.
Udgivet: (2002)

Organolithium-induced synthesis of unsaturated diols from epoxides of dihydrofurans and dihydropyrans
af: Hodgson, D, et al.
Udgivet: (2002)

Organolithium-induced synthesis of acyclic unsaturated amino alcohols from epoxides of dihydropyrroles and tetrahydropyridines
af: Hodgson, D, et al.
Udgivet: (2003)

Straightforward synthesis of alpha,beta-epoxysilanes from terminal epoxides by lithium 2,2,6,6-tetramethylpiperidide-mediated deprotonation-in situ silylation
af: Hodgson, D, et al.
Udgivet: (2002)

The reactivity of epoxides with lithium 2,2,6,6-tetramethylpiperidide in combination with organolithiums or grignard reagents.
af: Hodgson, D, et al.
Udgivet: (2007)

Asymmetric rearrangement of N-Boc 7-azanorbornene oxide: use of aryllithiums for enantioselective deprotonation
af: Hodgson, D, et al.
Udgivet: (1999)

Alkenes from terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide and organolithiums or grignard reagents.
af: Hodgson, D, et al.
Udgivet: (2004)

Terminal aziridines by alpha-deprotonation/electrophile trapping of N-protected aziridine.
af: Hodgson, D, et al.
Udgivet: (2008)

An enantioselective epoxide rearrangement - Claisen rearrangement approach to prostaglandins and (+)-iridomyrmecin
af: Hodgson, D, et al.
Udgivet: (1997)

Stereo- and Enantioselective Addition of Organolithiums to 2-Oxazolinylazetidines as a Synthetic Route to 2-Acylazetidines
af: Pantaleo Musci, et al.
Udgivet: (2019-09-01)

Organolithiums and lithium 2,2,6,6-tetramethylpiperidide in reductive alkylation of epoxides: Synthesis of (E)-alkenes [(E)-2-methyltetradeca-1,3- diene]
af: Hodgson, D, et al.
Udgivet: (2008)

Organolithium methods /
af: Wakefield, B. J. (Basil John), - 1934-
Udgivet: (1988)

Studies on organolithium-induced alkylative desymmetrisation of epoxides: synthesis of enantioenriched beta-amino cycloheptenols from 6,7-epoxy-8-azabicyclo[3.2.1]octanes
af: Hodgson, D, et al.
Udgivet: (2004)

Highly enantioselective rearrangement of quaternary carbon-containing meso-epoxides to allylic alcohols
af: Hodgson, D, et al.
Udgivet: (1996)

The chemistry of organolithium compounds /
af: Rappoport, Zvi, et al.
Udgivet: (2004)

The chemistry of organolithium compounds/
af: Wakefield, B. J. (Basil John), - 1934-
Udgivet: (1974)

Enantioselective CC Bond Formation Enhanced by Self-Assembly of Achiral Surfactants
af: Fumihiko Iwasaki, et al.
Udgivet: (2017-04-01)

Organocatalyzed enantioselective desymmetrization of aziridines and epoxides
af: Ping-An Wang
Udgivet: (2013-08-01)

Unsaturated 1,2-amino alcohols and ethers from aziridines and organolithiums.
af: Hodgson, D, et al.
Udgivet: (2004)

HIGHLY ENANTIOSELECTIVE REARRANGEMENT OF A MESO-EPOXIDE TO AN ALLYL ALCOHOL FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS - AN INTERNAL ALKOXIDE EFFECT
af: Hodgson, D, et al.
Udgivet: (1994)

Stereochemical aspects of organolithium compounds /
af: Gawley, Robert E.
Udgivet: (2010)

Erratum: Studies on organolithium-induced alkylative desymmetrisation of epoxides: Synthesis of enantioenriched β-amino cycloheptenols from 6,7-epoxy-8-azabicyclo[3.2.1]octanes (Tetrahedron (2004) 60 (5185))
af: Hodgson, D, et al.
Udgivet: (2004)

Studies on organolithium-induced alkylative desymmetrisation of epoxides: synthesis of enantioenriched beta-amino cycloheptenols from 6,7-epoxy-8-azabicyclo[3.2.1]octanes (vol, 60 pg, 5185 2004)
af: Hodgson, D, et al.
Udgivet: (2004)

Achiral bis-imine in combination with CoCl2: A remarkable effect on enantioselectivity of lipase-mediated acetylation of racemic secondary alcohol
af: K. Arunkumar, et al.
Udgivet: (2010-12-01)

Reactions of organolithium reagents with quinazoline derivatives
af: Gamal A. El-Hiti, et al.
Udgivet: (2012-05-01)

Enantioselective epoxidation of 1-hexene with sugar derived hydroperoxides
af: H.-J. Hamann, et al.
Udgivet: (2006-09-01)

Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers.
af: Hodgson, D, et al.
Udgivet: (2006)