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Note | Regular issue | Vol 45, No. 7, 1997, pp.1385-1390
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7796
Synthesis of Enantiomerically Pure Monosubstituted 1,2λ5-Oxaphospholanes. Synthesis of Z-Homoallylic Alcohls

Kentaro Okuma,* Yu-ichiro Tanaka, Syun-ichi Hirabayashi, Kosei Shioji, and Haruo Matsuyama

*Department of Chemistry, Faculty of Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

Enantiomerically pure 5-monosubstituted 1,2λ5-oxaphospholanes were synthesized by the reaction of sodium hydride with enantiomerically pure 3-hydroxyalkyltriphenylphosphonium salts. The reaction of 1,2λ5-oxaphospholanes with aldehydes afforded Z-rich homoallylic alcohols in nearly quantitative yields. The E:Z ratio of the products was in the range of 11:89-34:66.