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Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N-Alkyl β-Enamino Esters with Trichlorosilane and Water
Xinjun Wu1,2, Yang Li1, Chao Wang1, Li Zhou1, Prof.?Dr. Xiaoxia Lu1, Prof.?Dr. Jian Sun1
Keywords:amino esters;asymmetric reduction;enantioselectivity;organocatalysis;trichlorosilane
First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl β-enamino esters 1 to give N-alkyl β-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).