Synthesis of Highly Stereodefined Tetrasubstituted Acyclic All-Carbon Olefins via a Syn-Elimination Approach

• DOI: 10.1021/acs.orglett.7b03141
• Publication Date: 2017-11-08T16:10:51Z
• Authors: Ngiap-Kie Lim; Patrick Weiss; Beryl X. Li; Christina H. McCu...; Stephanie R. Hare; Bronwyn L. Bensema; Teresa A. Palazzo; Dean J. Tantillo; Haiming Zhang; Francis Gosselin
• Keywords: 01 natural sciences; 0104 chemical sciences

An efficient synthesis of stereodefined tetrasubstituted acyclic all-carbon olefins has been developed via a bis(2,6-xylyl)phosphate formation stereoenriched tertiary alcohols, followed by in situ syn-elimination the corresponding phosphates under mild conditions. This chemistry tolerates wide variety electronically and sterically diverse substrates generates desired high yields stereoselectivities (>95:5) most cases. stereocontrolled olefin applied to anticancer drug tamoxifen three steps from commercially available 1,2-diphenylbutan-1-one 97:3 stereoselectivity 78% overall yield.