Chemical communications

Sc (OTf) 3-catalyzed condensation of 2-alkyl-N-tosylaziridine with aldehydes or ketones: an efficient synthesis of 5-alkyl-1, 3-oxazolidines

B Kang, AW Miller, S Goyal, SBT Nguyen

Index: Kang, Byungman; Miller, Aaron W.; Goyal, Sandra; Nguyen, Sonbinh T. Chemical Communications, 2009 , # 26 p. 3928 - 3930

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Citation Number: 25

Abstract

Given the aforementioned impediments, the cycloaddition of aziridines to carbonyls in the presence of a Lewis acid (LA) is a more attractive strategy to 1,3-oxazolidine formation (Scheme 1). Surprisingly, very few reports have appeared on this method, 4,13,14 and with only modest scope and generality. For instance, because 2-alkyl-substituted aziridines are more resistant to LA-assisted ring-opening reactions, current reports are mostly limited to 2-aryl-substituted ...