Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenylboron Reagents

A hybrid transition metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenylboron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-08, Vol.58 (40), p.14245-14249
Main Authors: Chierchia, Matteo, Xu, Peilin, Lovinger, Gabriel J., Morken, James P.
Format: Article
Language:English
Online Access:Get full text
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Summary:A hybrid transition metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenylboron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yields and high enantioselectivities in both manifolds. A Radical Hydrid: Dicarbofunctionalization of vinylB(pin) is accomplished through the use of a Ni-based chiral catalyst. The reaction employs alkyl halide and organozinc reagents and can be accomplished with good levels of enantioselectivity in either an intra- or intermolecular fashion.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201908029