Highly Stereoselective Synthesis of trans-3-Chloro-β-lactams from Imines and Mixed Chloroacetyl and Nitroacetyl Chlorides  

作　　者：QI Heng-zhen MO Shan-yan XU Jia-xi 

机构地区：[1]State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. China

出　　处：《Chemical Research in Chinese Universities》2011年第6期958-962,共5页高等学校化学研究（英文版）

基　　金：Supported by the National Natural Science Foundation of China(Nos.20772005,20972013);the Beijing Natural Science Foundation,China(No.2092022);the Specialized Research Fund for the Doctoral Program of Higher Education,Ministry of Education of China

摘　　要：A series of trans-3-chloro-β-lactams was synthesized stereospecifically from imines and chloroacetyl chloride or a mixture of chloroacetyl chloride and nitroacetyl chloride, prepared from vinylidene chloride and a mixture of concentrated nitric acid and sulfuric acid, in the presence of triethylamine. The reaction of vinylidene chloride and the mixed acid was investigated. The formation mechanism of chloroacetyl chloride and nitroacetyl chloride and their reaction process with imines were proposed.A series of trans-3-chloro-β-lactams was synthesized stereospecifically from imines and chloroacetyl chloride or a mixture of chloroacetyl chloride and nitroacetyl chloride, prepared from vinylidene chloride and a mixture of concentrated nitric acid and sulfuric acid, in the presence of triethylamine. The reaction of vinylidene chloride and the mixed acid was investigated. The formation mechanism of chloroacetyl chloride and nitroacetyl chloride and their reaction process with imines were proposed.

关 键 词：Β-LACTAM Chloroacetyl chloride Staudinger reaction STEREOSELECTIVITY 

分 类 号：TQ463.24[化学工程—制药化工] TQ153.15