Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes

Jia, Tao, Smith, Marshall J., Pulis, Alexander P., Perry, Gregory J.P. and Procter, David J. (2019) Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes. ACS Catalysis, 9 (8), 6744-6750. (doi:10.1021/acscatal.9b01911).

Record type: Article

Abstract

A multicomponent copper-catalyzed enantio- A nd regioselective borocyanation of 1-aryl-1,3-butadienes has been developed. The method provides access to functionalized allylic nitriles in up to 90% yield and 94% ee and thus overcomes some of the long-standing problems associated with the enantioselective insertion of cyano groups into unsaturated organic molecules. Both boron and cyano functionalities can be used as handles for selective manipulation. ©

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Published date: 2 August 2019

Additional Information: Funding Information: We thank the EPSRC (Established Career Fellowship to D.J.P.; EP/M005062/1), the Royal Society (Newton International Fellowship to T.J.), and the University of Manchester (Lectureships to A.P.P. and G.J.P.P). We also thank the X-ray Crystallography Service at the University of Manchester. Publisher Copyright: Copyright © 2019 American Chemical Society.

Keywords: 1,3-dienes, asymmetric catalysis, borylation, copper, cyanation