Diastereoselective one-step synthesis of functionalized cis-aziridinyl alcohols from oxiranyl carbaldimines.
[reaction: see text]. 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.
Bilke
Julia Luzia
JL
Organisch-Chemisches Institut der Westfälischen Wilhelms-Universität Münster, Germany.
Dzuganova
Monika
M
Fröhlich
Roland
R
Würthwein
Ernst-Ulrich
EU