Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

α-Lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines undergo eliminative cross-coupling with α-lithio ethers, to give convergent access to allylic alcohols and allylic amines, respectively. The process can be considered as proceeding by selective strain-relieving attack (ring-opening)...

Descripción completa

Detalles Bibliográficos
Autores principales: Fleming, Matthew J, Hodgson, David M
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8450947/
https://www.ncbi.nlm.nih.gov/pubmed/34621400
http://dx.doi.org/10.3762/bjoc.17.155
_version_ 1784569746567462912
author Fleming, Matthew J
Hodgson, David M
author_facet Fleming, Matthew J
Hodgson, David M
author_sort Fleming, Matthew J
collection PubMed
description α-Lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines undergo eliminative cross-coupling with α-lithio ethers, to give convergent access to allylic alcohols and allylic amines, respectively. The process can be considered as proceeding by selective strain-relieving attack (ring-opening) of the lithiated three-membered heterocycle by the lithio ether and then selective β-elimination of lithium alkoxide.
format Online
Article
Text
id pubmed-8450947
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-84509472021-10-06 Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines Fleming, Matthew J Hodgson, David M Beilstein J Org Chem Letter α-Lithiated terminal epoxides and N-(tert-butylsulfonyl)aziridines undergo eliminative cross-coupling with α-lithio ethers, to give convergent access to allylic alcohols and allylic amines, respectively. The process can be considered as proceeding by selective strain-relieving attack (ring-opening) of the lithiated three-membered heterocycle by the lithio ether and then selective β-elimination of lithium alkoxide. Beilstein-Institut 2021-09-10 /pmc/articles/PMC8450947/ /pubmed/34621400 http://dx.doi.org/10.3762/bjoc.17.155 Text en Copyright © 2021, Fleming and Hodgson https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Letter
Fleming, Matthew J
Hodgson, David M
Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
title Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
title_full Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
title_fullStr Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
title_full_unstemmed Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
title_short Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
title_sort allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8450947/
https://www.ncbi.nlm.nih.gov/pubmed/34621400
http://dx.doi.org/10.3762/bjoc.17.155
work_keys_str_mv AT flemingmatthewj allylicalcoholsandaminesbycarbenoideliminativecrosscouplingusingepoxidesoraziridines
AT hodgsondavidm allylicalcoholsandaminesbycarbenoideliminativecrosscouplingusingepoxidesoraziridines

Ejemplares similares