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. 2018 Jan 10;140(1):139-142.
doi: 10.1021/jacs.7b11707. Epub 2017 Dec 20.

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

Julie L Hofstra  1 , Alan H Cherney  1 , Ciara M Ordner  1 , Sarah E Reisman  1
Affiliations

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

Julie L Hofstra et al. J Am Chem Soc. .

Abstract

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.

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Figures

Figure 1
Figure 1
Synthesis of Chiral Allylic Silanes by Enantioselective Ni-Catalyzed Reductive Cross-Coupling
Scheme 1
Scheme 1
Reactions of Oxygen-Based Electrophiles
Scheme 2
Scheme 2
Stereospecific Reactions of Chiral Allylic Silanes
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