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. 2014 Oct 15;136(41):14365-8.
doi: 10.1021/ja508067c. Epub 2014 Oct 1.

Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles

Alan H Cherney  1 , Sarah E Reisman
Affiliations

Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles

Alan H Cherney et al. J Am Chem Soc. .

Abstract

A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.

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Figures

Figure 1
Figure 1
Catalytic asymmetric synthesis of alkenes bearing aryl-substituted allylic stereogenic centers.
Scheme 1
Scheme 1. Further Investigation of Reaction Scope
Run with 15 mol % NiCl2(dme) and 16 mol % L6.
Scheme 2
Scheme 2. Mechanistic Investigations
See this image and copyright information in PMC

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