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Communication | Regular issue | Vol 26, No. 2, 1987, pp.373-376
Published online, 1st January, 1970
DOI: 10.3987/R-1987-02-0373
Diastereoselective Synthesis of trans-4,5-Disubstituted Oxazolidin-2-ones and Vicinal Amino Alcohols through Alkylation of N-Acyliminium Ion Intermediates

Shinzo Kano, Yoko Yuasa, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Treatment of 5-substituted 4-ethoxyoxazolidin-2-ones (10a-f, 13a,b) with allyltrimethylsilane in the presence of titanium tetrachloride gave the corresponding trans-4,5-disubstituted oxazolidin-2-ones (14a-f, 16a,b), respectively, with high diastereoselectivity. Methallylation of 13a,b with methallyltrimethylsilane yielded 16c,d, respectively. Ring cleavage of 14a-f afforded the corresponding three vicinal amino alcohols (17a-f), respectively.