862884-85-3Relevant articles and documents
Diastereoselective one-step synthesis of functionalized cis-aziridinyl alcohols from oxiranyl carbaldimines
Bilke, Julia Luzia,Dzuganova, Monika,Froehlich, Roland,Wuerthwein, Ernst-Ulrich
, p. 3267 - 3270 (2007/10/03)
(Chemical Equation Presented) Upon treatment with lithiumorganic nucleophiles, trans-configured oxiranyl carbaldimines are transformed into anti-configured cis-aziridinyl alcohols with excellent diastereoselectivity. This conversion may be explained by a new type of the aza-Payne rearrangement, including first a nucleophilic attack on the imine carbon atom with diastereofacial differentiation followed by an intramolecular nucleophilic opening of the oxiranyl ring with simultaneous formation of the aziridine ring.