Simmons-Smith Reactions of Fluoroallyl Alcohol Derivatives

Tsutomu MORIKAWA; Hirofumi SASAKI; Kazuya MORI; Motoo SHIRO; Takeo TAGUCHI

doi:10.1248/cpb.40.3189

Tsutomu MORIKAWA, Hirofumi SASAKI, Kazuya MORI, Motoo SHIRO, Takeo TAGUCHI

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Keywords: Simmons-Smith reaction, cyclopropanation, fluorine, allyl alcohol, cyclopropane, diastereoselectivity, optically active

JOURNAL FREE ACCESS

1992 Volume 40 Issue 12 Pages 3189-3193

DOI https://doi.org/10.1248/cpb.40.3189

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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 (R)-2, 3-O-isopropylidene glyceraldehyde was successfully carried out to give the optically active fluorocyclopropane derivative in high selectivity (>98% de).

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