One pot synthesis of homochiral aziridines and aminoalcohols from homochiral 1, 2-cyclic sulfates
BB Lohray, Y Gao, KB Sharpless
Index: Lohray, B. Bhushan; Gao, Yun; Sharpless, K. Barry Tetrahedron Letters, 1989 , vol. 30, # 20 p. 2623 - 2626
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Citation Number: 119
Abstract
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.
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