Tetrahedron Letters

One pot synthesis of homochiral aziridines and aminoalcohols from homochiral 1, 2-cyclic sulfates

BB Lohray, Y Gao, KB Sharpless

文献索引：Lohray, B. Bhushan; Gao, Yun; Sharpless, K. Barry Tetrahedron Letters, 1989 , vol. 30, # 20 p. 2623 - 2626

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被引用次数: 119

摘要

Abstract Preparations of homochiral N-substituted aziridines and aminoalcohols from 1, 2- cyclic sulfates are reported. Primary amines react with cyclic sulfates to give β-aminosulfates which can be converted either to aziridines or to aminoalcohols by treatment with base or aqueous acid, respectively. Reaction of cyclic sulfates with azide followed by LiAlH 4 reduction/cyclization yields N-unsubstituted aziridines.