Scalable synthesis of N-acylaziridines from N-tosylaziridines

H Rubin, J Cockrell, JB Morgan

Index: Rubin, Heather; Cockrell, Jennifer; Morgan, Jeremy B. Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8865 - 8871

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Citation Number: 5

Abstract

N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaziridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono-and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently ...