Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates

A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form β-disubstituted acrylates is reported. The addition occurred in a formal syn-hydroalkylation mode. The syn stereoselectivity was excellent regardless o...

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Autores principales: Wakamatsu, Takamichi, Nagao, Kazunori, Ohmiya, Hirohisa, Sawamura, Masaya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685882/
https://www.ncbi.nlm.nih.gov/pubmed/26734092
http://dx.doi.org/10.3762/bjoc.11.265
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author Wakamatsu, Takamichi
Nagao, Kazunori
Ohmiya, Hirohisa
Sawamura, Masaya
author_facet Wakamatsu, Takamichi
Nagao, Kazunori
Ohmiya, Hirohisa
Sawamura, Masaya
author_sort Wakamatsu, Takamichi
collection PubMed
description A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form β-disubstituted acrylates is reported. The addition occurred in a formal syn-hydroalkylation mode. The syn stereoselectivity was excellent regardless of the substrate structure. A variety of functional groups were compatible with the conjugate addition.
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spelling pubmed-46858822016-01-05 Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates Wakamatsu, Takamichi Nagao, Kazunori Ohmiya, Hirohisa Sawamura, Masaya Beilstein J Org Chem Full Research Paper A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form β-disubstituted acrylates is reported. The addition occurred in a formal syn-hydroalkylation mode. The syn stereoselectivity was excellent regardless of the substrate structure. A variety of functional groups were compatible with the conjugate addition. Beilstein-Institut 2015-12-04 /pmc/articles/PMC4685882/ /pubmed/26734092 http://dx.doi.org/10.3762/bjoc.11.265 Text en Copyright © 2015, Wakamatsu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Wakamatsu, Takamichi
Nagao, Kazunori
Ohmiya, Hirohisa
Sawamura, Masaya
Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
title Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
title_full Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
title_fullStr Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
title_full_unstemmed Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
title_short Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
title_sort copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685882/
https://www.ncbi.nlm.nih.gov/pubmed/26734092
http://dx.doi.org/10.3762/bjoc.11.265
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