Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling

An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of...

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Bibliographic Details
Published in:	Journal of the American Chemical Society Vol. 140; no. 1; pp. 139 - 142
Main Authors:	Hofstra, Julie L, Cherney, Alan H, Ordner, Ciara M, Reisman, Sarah E
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 10-01-2018
Subjects:	Allyl Compounds - chemical synthesis Allyl Compounds - chemistry Catalysis Molecular Structure Nickel - chemistry Oxidation-Reduction Silanes - chemical synthesis Silanes - chemistry Stereoisomerism
Online Access:	Get full text
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Summary:	An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi–Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0002-7863 1520-5126
DOI:	10.1021/jacs.7b11707