Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Racemic Secondary Allylic Chlorides with Alkylzincs

The transition metal-catalyzed enantioselective coupling of allylic electrophiles with carbon nucleophiles has been the focus of intense investigation.5 Salient examples include palladium-catalyzed couplings with enolates, nickel-catalyzed couplings with Grignard reagents, and copper-catalyzed coupl...

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Bibliographic Details
Main Authors: Lou, Sha, Fu, Gregory C.
Other Authors: Massachusetts Institute of Technology. Department of Chemistry
Format: Article
Language:en_US
Published: Organic Syntheses, Inc. 2011
Online Access:http://hdl.handle.net/1721.1/67662
Description
Summary:The transition metal-catalyzed enantioselective coupling of allylic electrophiles with carbon nucleophiles has been the focus of intense investigation.5 Salient examples include palladium-catalyzed couplings with enolates, nickel-catalyzed couplings with Grignard reagents, and copper-catalyzed couplings with Grignard and diorganozinc reagents.6 Despite impressive progress, the development of methods that have broader scope with respect to the nucleophile, as well as improved functional-group compatibility, persist as important challenges.