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Paper | Special issue | Vol 37, No. 1, 1994, pp.413-423
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S26
Preparation of Optically Active Tricyclic 1,4-Dioxepin-5-one Derivatives and Its Application to Asymmetric Alkylation

Keisuke Kato, Hiroshi Suemune, and Kiyoshi Sakai*

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan

Abstract

Chiral hicyclic α,β-unsaturated lactones (6a,b and 8a,b) were easily synthesized from chiral cyclic diols (2-4) and cyclic β-keto esters (1a,b). Alkylation of 8b proceeded in a highly diastereoselective manner to afford a quaternary carbon.