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Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes

Liela Bayeh-Romero and Stephen L. Buchwald*

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

L. Bayeh-Romero, S. L. Buchwald, J. Am. Chem. Soc., 2019, 141, 13788-13794.

DOI: 10.1021/jacs.9b07582

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An efficient enantio- and chemoselective copper hydride catalyzed semireduction of conjugated enynes provides 1,3-disubstituted allenes using water as the proton source. This protocol tolerates various functional groups including keto, ester, amino, halo, and hydroxyl groups.

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proposed mechanism

Key Words

semi-reduction of 1,3-enynes, silanes, CuH

ID: J48-Y2019