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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Detalles Bibliográficos
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
Descripción
Sumario: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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