Novel Method for the Enantioselective Synthesis of β-Lactams  

作　　者：YUAN Qing JIAN Shan-zhong WANG Yan-guang 

机构地区：[1]Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China

出　　处：《Chemical Research in Chinese Universities》2008年第1期58-64,共7页高等学校化学研究（英文版）

基　　金：National Natural Science Foundation of China(No. 20272051);Natural Science Foundation of Zhejiang Province, China(No. R404109)

摘　　要：A novel method for the enantioselective synthesis of β-lactams is described in this study. 2,3-Dihydrobenzooxazin-4-one derived from salicylamide and L-menthone was used as the chiral auxiliary, which reacted with a-bromo-acyl bromides in the presence of pyridine to give carboximides 2. The stereo-controlled Reformatsky-type reactions of carboximides with imines yielded the corresponding trans β-lactams with high enantioselectivities（e.e. 75%-86%） and high chemical yields（63%-85%）, meanwhile, the chiral auxiliary dihydrobenzooxazin-4-one was released and recovered.A novel method for the enantioselective synthesis of β-lactams is described in this study. 2,3-Dihydrobenzooxazin-4-one derived from salicylamide and L-menthone was used as the chiral auxiliary, which reacted with a-bromo-acyl bromides in the presence of pyridine to give carboximides 2. The stereo-controlled Reformatsky-type reactions of carboximides with imines yielded the corresponding trans β-lactams with high enantioselectivities（e.e. 75%-86%） and high chemical yields（63%-85%）, meanwhile, the chiral auxiliary dihydrobenzooxazin-4-one was released and recovered.

关 键 词：Β-LACTAMS ENANTIOSELECTIVE Chiralauxiliary Reformatskyreaction 

分 类 号：R97[医药卫生—药品] O636.1[医药卫生—药学]