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Enantioselective Olefin Hydrocyanation without Cyanide

Alexander W. Schuppe, Gustavo M. Borrajo-Calleja and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

A. W. Schuppe, G. M. Borrajo-Calleja, S. L. Buchwald, J. Am. Chem. Soc., 2019, 141, 18668-18672.

DOI: 10.1021/jacs.9b10875 (free Supporting Information)


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Abstract

Oxazoles function as nitrile equivalents in a cyanide-free dual Pd/CuH-catalyzed protocol for the asymmetric Markovnikov hydrocyanation of vinyl arenes and the anti-Markovnikov hydrocyanation of terminal olefins. After an initial hydroarylation process, the oxazole substructure was deconstructed using a mild [4 + 2]/retro-[4 + 2] sequence to afford the enantioenriched nitrile product.

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Key Words

nitriles, silanes


ID: J48-Y2019