Kinetic Resolution of trans-2,3-Aziridinyl Alcohols via Hydroxyl Directed Regio- and Enantioselective Ring Opening Reactions

An efficient kinetic resolution of racemic trans-2,3-aziridinyl alcohols is established via zinc catalyzed ring opening reactions with various amines as the nucleophiles. The directing effect of the hydroxyl group and the precise enantiodiscrimination by dinuclear zinc cooperative catalyst are the keys to success of high regioselectivity and enantioselectivity. A range of enantioenriched vicinal diamines and trans-2,3-aziridinyl alcohols were obtained in good yields with excellent ee values. To the best of our knowledge, this is the first example of directed enantioselective nucleophilic ring opening reactions of 2,3-aziridinyl alcohols.

Automated summary

An efficient kinetic resolution of racemic trans-2,3-aziridinyl alcohols is achieved through zinc catalyzed ring opening reactions with different amines as nucleophiles. The directing effect of the hydroxyl group and the precise enantiodiscrimination by a dinuclear zinc cooperative catalyst are crucial for high regioselectivity and enantioselectivity. Various enantioenriched vicinal diamines and trans-2,3-aziridinyl alcohols are obtained in good yields with excellent ee values. This study represents the first example of directed enantioselective nucleophilic ring opening reactions of 2,3-aziridinyl alcohols.