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Communication | Regular issue | Vol 38, No. 8, 1994, pp.1751-1756
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6801
Diastereoselective Addition of Allyltriphenylstannane to 3-Sulfinylfurfural Mediated by Titanium(IV) Tetrachloride and Tin(IV) Tetrachloride

Yoshitsugu Arai* Tsutomu Masuda, Yukio Masaki, and Toru Koizumi

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

The addition of allyltriphenylstannane to 3-sulfinylfurfural (3) in the presence of titanium(IV) tetrachloride proceeded with high diastereoselectivity to give the furyl alcohol (6), whereas the similar treatment with tin(IV) tetrachloride afforded the other diastereoisomeric alcohol (7), exclusively.