Enantioselective insertion of carbenoids into N-H bonds catalyzed by chiral bicyclobisoxazoline copper(I) complexes

Chiral copper(I)-bicyclobisoxazoline complexes were found to catalyze the insertion of alpha-diazocarbonyl compounds into N-H bonds of aniline derivatives. The insertion reactions proceeded with high yields (78-99%) and enantioselectivities of up to 81% for the different alpha-diazopropionates. A predominant effect of the nature and the position of the substituents on the enantiocontrol of the reaction was observed. (C) 2015 Elsevier Ltd. All rights reserved.