Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.

This article compares the diastereoselective epoxidation of acyclic and cyclic allylic alcohols, with the chemo- and diastereoselective olefinic oxidation of a range of acyclic and cyclic allylic amines. The diastereoselectivity in these systems is compared and a discussion about the origin of this...

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Main Authors: Davies, S, Fletcher, A, Thomson, J
Format: Journal article
Language:English
Published: Royal Society of Chemistry 2014
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author Davies, S
Fletcher, A
Thomson, J
author_facet Davies, S
Fletcher, A
Thomson, J
author_sort Davies, S
collection OXFORD
description This article compares the diastereoselective epoxidation of acyclic and cyclic allylic alcohols, with the chemo- and diastereoselective olefinic oxidation of a range of acyclic and cyclic allylic amines. The diastereoselectivity in these systems is compared and a discussion about the origin of this high diastereocontrol is also presented. The ammonium directed epoxidation methodology has been extended to more complex substrates and representative applications of this protocol in natural product synthesis are also summarised.
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spelling oxford-uuid:f4b32790-246d-4651-81d0-c61c3972f0b52022-03-27T12:21:44ZHydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:f4b32790-246d-4651-81d0-c61c3972f0b5EnglishSymplectic Elements at OxfordRoyal Society of Chemistry2014Davies, SFletcher, AThomson, JThis article compares the diastereoselective epoxidation of acyclic and cyclic allylic alcohols, with the chemo- and diastereoselective olefinic oxidation of a range of acyclic and cyclic allylic amines. The diastereoselectivity in these systems is compared and a discussion about the origin of this high diastereocontrol is also presented. The ammonium directed epoxidation methodology has been extended to more complex substrates and representative applications of this protocol in natural product synthesis are also summarised.
spellingShingle Davies, S
Fletcher, A
Thomson, J
Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.
title Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.
title_full Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.
title_fullStr Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.
title_full_unstemmed Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.
title_short Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines.
title_sort hydrogen bond directed epoxidation diastereoselective olefinic oxidation of allylic alcohols and amines
work_keys_str_mv AT daviess hydrogenbonddirectedepoxidationdiastereoselectiveolefinicoxidationofallylicalcoholsandamines
AT fletchera hydrogenbonddirectedepoxidationdiastereoselectiveolefinicoxidationofallylicalcoholsandamines
AT thomsonj hydrogenbonddirectedepoxidationdiastereoselectiveolefinicoxidationofallylicalcoholsandamines