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 2018-01, Vol.140 (1), p.139-142
Main Authors: Hofstra, Julie L, Cherney, Alan H, Ordner, Ciara M, Reisman, Sarah E
Format: Article
Language:English
Subjects:
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Catalysis
cross-coupling reactions
enantioselectivity
moieties
Molecular Structure
Nickel - chemistry
optical isomerism
Oxidation-Reduction
silanes
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
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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.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.7b11707