文献类型：期刊文献

英文题名：Stereoselective or Exclusive Synthesis of Ethyl (Z)-2-(2-Substituted-thiazol-4-yl) pent-2-enoates from Ethyl (E/Z)-2-(2-Bromoacetyl) pent-2-enoate

作者：Zhai, Jiao-Jiao[1];Jiang, Jian-An[1];Zhang, Shun-Li[1];Chen, Cheng[1];Liu, Hong-Wei[1];Liao, Dao-Hua[1];Ji, Ya-Fei[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

年份：2013

卷号：24

期号：11

起止页码：1399

外文期刊名：SYNLETT

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000320576600012)，CCR-EXPANDED(收录号:WOS:000320576600012)】；

基金：The authors thank the National Natural Science Foundation of China (Project No. 21176074) for financial supports.

语种：英文

外文关键词：thiazoles; stereocontrolled reaction; E/Z isomerization; antibiotic; cefcapene pivoxil

摘要：A stereoselective or exclusive approach to a series of ethyl (Z)-2-(2-substituted-thiazol-4-yl) pent-2-enoates from ethyl (E/Z)-2-(2-bromoacetyl) pent-2-enoate and thioureas or thioamides was reported in good yields. This approach involves a quaternary carbon stereocontrolled cis-configuration formation, and opportunely blocking a potential E/Z isomerization. The practical applicability was highlighted by the synthesis of (Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)pent-2-enoic acid, a commercially important side-chain material of cefcapene pivoxil, in a two-step procedure.