Asymmetric hydroazidation ofα-substituted vinyl ketones catalyzed by chiral primary amine  

作　　者：Zai-Kun Xue Nian-Kai Fu San-Zhong Luo 

机构地区：[1]Beijing National Laboratory for Molecular Sciences(BNLMS),CAS Key Laboratory of Molecular Recognition and Function,Institute of Chemistry,Chinese Academy of Sdences,Beijing 100190,China

出　　处：《Chinese Chemical Letters》2017年第5期1083-1086,共4页中国化学快报（英文版）

基　　金：National Natural Science Foundation of China(NSFC Nos.21390400,21521002 and 21502198);the Ministry of Science and Technology,Chinese Academy of Sciences(No.QYZDJSSW-SLH023)for generous financial support;supported by National Program for Support of Top-notch Young Professionals,CAS Youth Innovation Promotion Association and CAS onehundred talented program(D)

摘　　要：We report herein the first example of asymmetric hydroazidation of α-substituted vinyl ketones by using chiral primary amines as the catalysts.A simple chiral primary-tertiary diamine catalyst derived from lphenylalanine was found to readily promote this aza-Michael addition reaction with enamine protonation as the key stereogenic step,thus enabling the effective synthesis of α-chiral β-azido ketones with good yields and moderate enantioselectivities.We report herein the first example of asymmetric hydroazidation of α-substituted vinyl ketones by using chiral primary amines as the catalysts.A simple chiral primary-tertiary diamine catalyst derived from lphenylalanine was found to readily promote this aza-Michael addition reaction with enamine protonation as the key stereogenic step,thus enabling the effective synthesis of α-chiral β-azido ketones with good yields and moderate enantioselectivities.

关 键 词：Chiral primary amine catalysis Hydroazidation Enamine protonation α-Substituted vinyl ketones Aza-Michael addition Chiral β-azido ketones 

分 类 号：O621.251[理学—有机化学]