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Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates.

ABSTRACT: A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form ?-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.

SUBMITTER: Wakamatsu T

PROVIDER: S-EPMC4685882 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates.

Wakamatsu Takamichi T Nagao Kazunori K Ohmiya Hirohisa H Sawamura Masaya M

Beilstein journal of organic chemistry 20151204

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. ...[more]

PMID: 26734092

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