Deprotonation-electrophile trapping of terminal epoxides.

Deprotonation-electrophile trapping of terminal epoxides.

Organolithium-induced deprotonation of terminal epoxides in the presence of appropriate diamine ligands allows trapping with a range of electrophiles, yielding functionalised di- and tri-substituted epoxides in good yields and with control of stereochemistry at the epoxide.

Manylion Llyfryddiaeth
Prif Awduron:	Hodgson, D, Kirton, E, Miles, S, Norsikian, S, Reynolds, N, Coote, S
Fformat:	Journal article
Iaith:	English
Cyhoeddwyd:	2005

Eitemau Tebyg

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

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

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

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

Enantioselective alpha-deprotonation of epoxides.
gan: Hodgson, D
Cyhoeddwyd: (2001)

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

Substituted epoxides by lithiation of terminal epoxides.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2004)

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

Epoxydisilanes by direct double silylation of terminal epoxides
gan: Hodgson, D, et al.
Cyhoeddwyd: (2004)

Substituted aziridines by lithiation-electrophile trapping of terminal aziridines.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2005)

Ligand effects in the organolithium-mediated enantioselective alpha-deprotonation of achiral epoxides
gan: Hodgson, D, et al.
Cyhoeddwyd: (1997)

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

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

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

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

Lithiation: Electrophile trapping of simple aziridine building blocks
gan: Hughes, S, et al.
Cyhoeddwyd: (2007)

Alkenes from β-lithiooxyphosphonium ylides generated by trapping α-lithiated terminal epoxides with triphenylphosphine.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2012)

Intramolecular cyclopropanation of unsaturated terminal epoxides.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2004)

Enamines from terminal epoxides and hindered lithium amides.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2004)

Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2007)

Electrophile dependent mechanisms in the asymmetric trapping of α-lithio-N-(tert-butoxythiocarbonyl)azetidine
gan: Delany, PK, et al.
Cyhoeddwyd: (2020)

Asymmetric synthesis of alpha-alkylated aldehydes using terminal epoxide-derived chiral enamines.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2008)

α-Lithiation-electrophile trapping of N-thiopivaloylazetidin-3-ol: stereoselective synthesis of 2-substituted 3-hydroxyazetidines.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2013)

Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2014)

Highly enantioenriched 2-azabenzonorbornenes from 7-azabenzonorbornadienes by asymmetric hydroboration-oxidation and tandem deoxygenation-rearrangement-electrophile trapping
gan: Hodgson, D, et al.
Cyhoeddwyd: (2006)

Lithiation-electrophilic substitution of N-thiopivaloylazetidine.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2010)

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

2-Ene-1,4-diols by dimerization of terminal epoxides using hindered lithium amides.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2005)

Electrophilic fluorocyclization vs. electrophilic fluorodesilylation
gan: Pacheco, M, et al.
Cyhoeddwyd: (2005)

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

Thieme Chemistry Journal Awardees - Where Are They Now? Synthesis of (-)-Cubebol by Intramolecular Cyclopropanation of a Terminal Epoxide
gan: Hodgson, D, et al.
Cyhoeddwyd: (2009)

Accessible sugars as asymmetric olefin epoxidation organocatalysts: glucosaminide ketones in the synthesis of terminal epoxides.
gan: Boutureira, O, et al.
Cyhoeddwyd: (2009)

Dimerization of lithiated terminal aziridines.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2006)

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

syn-β-Hydroxyallylic silanes from terminal epoxide α-lithiation-silylation and alkenylation: application to the tetrahydrofuran portion of the lytophilippines.
gan: Hodgson, D, et al.
Cyhoeddwyd: (2012)

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

Recent developments in the chemistry of lithiated epoxides
gan: Hodgson, D, et al.
Cyhoeddwyd: (2002)

Metalated Epoxides and Aziridines in Synthesis
gan: Hodgson, D, et al.
Cyhoeddwyd: (2006)

Functionalized alkenes from epoxides
gan: Hodgson, D, et al.
Cyhoeddwyd: (2004)

Enantioselective desymmetrisation of achiral epoxides
gan: Hodgson, D, et al.
Cyhoeddwyd: (1996)