A convergent method for the stereoselective synthesis of trisubstituted alkenes

SF Martin, D Daniel, RJ Cherney…

Index: Martin, Stephen F.; Daniel, Dilon; Cherney, Robert J.; Liras, Spiros Journal of Organic Chemistry, 1992 , vol. 57, # 9 p. 2523 - 2525

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Citation Number: 32

Abstract

Summary: A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed. The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent. Treatment of 9 with carbon disulfide and methyl iodide gave the intermediate allylic xanthates 10 that underwent facile [3, 3]- sigmatropic rearrangement to give the dithiocarbonates 11 and 12, radical reduction of ...