Journal
ORGANIC LETTERS
Volume 19, Issue 22, Pages 6212-6215Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03141
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An efficient synthesis of stereodefined tetrasubstituted acyclic all-carbon olefins has been developed via a bis(2,6-xylyl)phosphate formation of stereoenriched tertiary alcohols, followed by in situ syn-elimination of the corresponding phosphates under mild conditions. This chemistry tolerates a wide variety of electronically and sterically diverse substrates and generates the desired tetrasubstituted olefins, in high yields and stereoselectivities (>95:5) in most cases. This stereocontrolled olefin synthesis has been applied to the synthesis of anticancer drug tamoxifen in three steps from commercially available 1,2-diphenylbutan-l-one in 97:3 stereoselectivity and 78% overall yield.
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