Simmons-Smith Reactions of Fluoroallyl Alcohol Derivatives

Abstract

Simmons-Smith reactions of fluoroallyl alcohols and their derivatives with excess Zn-Cu and CH2I2 or Et2Zn and CH2I2 provided fluorocyclopropane derivatives. Diastereoselective cyclopropanation of the fluoroallyl alcohol derivative obtained from (/?)-2,3-0-isopropylidene glyceraldehyde was successfully carried out to give the optically active fluorocyclopropane derivative in high selectivity (> 98% de). © 1992, The Pharmaceutical Society of Japan. All rights reserved.