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Communication | Special issue | Vol 52, No. 3, 2000, pp.1071-1074
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S135
Modified Cyclization of Enantio-enriched α-Homoallyloxyalkyllithiums Generated by Sn-Li Transmetallation: Effects of Additives and Structural Requirement

Nobuyuki Komine, Katsuhiko Tomooka,* and Takeshi Nakai*

*Department of Applied Chemistry, Graduate School of Science and Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan

Abstract

The titled cyclization, when performed in the presence of lithium chloride, afforded an improved yield of the enantio-enriched 2,3-trans-disubstituted tetrahydrofuran derivative in high diastereoselectivity, whereas a similar cycization in the presence of zinc bromide gave the 2,3-cis isomer as the major product in lower enantiopurity.