Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides

[Image: see text] The first catalytic, highly C3-selective, stereosepecific ring-opening reaction of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides has been accomplished. This process was efficiently promoted by W-salts, and the developed method was applicable to various epoxides with diverse N- and...

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Autores principales: Wang, Chuan, Yamamoto, Hisashi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4333593/
https://www.ncbi.nlm.nih.gov/pubmed/24773529
http://dx.doi.org/10.1021/ja5029809
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author Wang, Chuan
Yamamoto, Hisashi
author_facet Wang, Chuan
Yamamoto, Hisashi
author_sort Wang, Chuan
collection PubMed
description [Image: see text] The first catalytic, highly C3-selective, stereosepecific ring-opening reaction of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides has been accomplished. This process was efficiently promoted by W-salts, and the developed method was applicable to various epoxides with diverse N- and O-nucleophiles affording the products in good to excellent yields (up to 95%) and generally with high regioselectivities (C3:C2 up to >99:1).
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spelling pubmed-43335932015-04-29 Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides Wang, Chuan Yamamoto, Hisashi J Am Chem Soc [Image: see text] The first catalytic, highly C3-selective, stereosepecific ring-opening reaction of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides has been accomplished. This process was efficiently promoted by W-salts, and the developed method was applicable to various epoxides with diverse N- and O-nucleophiles affording the products in good to excellent yields (up to 95%) and generally with high regioselectivities (C3:C2 up to >99:1). American Chemical Society 2014-04-29 2014-05-14 /pmc/articles/PMC4333593/ /pubmed/24773529 http://dx.doi.org/10.1021/ja5029809 Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Wang, Chuan
Yamamoto, Hisashi
Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides
title Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides
title_full Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides
title_fullStr Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides
title_full_unstemmed Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides
title_short Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides
title_sort tungsten-catalyzed regioselective and stereospecific ring opening of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4333593/
https://www.ncbi.nlm.nih.gov/pubmed/24773529
http://dx.doi.org/10.1021/ja5029809
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AT yamamotohisashi tungstencatalyzedregioselectiveandstereospecificringopeningof23epoxyalcoholsand23epoxysulfonamides

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