Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to ( Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials.

Author(s) Chen, F.; Chen, Y.; Cao, H.; Xu, Q.; Yu, L.
Journal J Org Chem
Date Published 2018 Oct 24
Abstract

Copper-catalyzed coupling of Grignard reagents with pent-1-en-4-yn-3-yl benzoates occurs regioselectively at the terminal alkenyl carbon rather than the alkynyl site, leading to the stereoselective formation of unexpected ( Z) -1,5-disubstituted pent-3-en-1-ynes without generation of the initially expected alkenyl allene products. By using easily accessible starting materials, this reaction can provide direct access to thermodynamically unfavorable Z-configured enynes, which widely exist in many bioactive natural products, such as the anti-inflammatory components in henna.

DOI 10.1021/acs.joc.8b02275
ISSN 1520-6904
Citation Chen F, Chen Y, Cao H, Xu Q, Yu L. Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to ( Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials. J Org Chem. 2018.

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