Jiao-Jiao Zhai, Jian'an Jiang, Shunli Zhang
Jun 5, 2013
Citations
0
Influential Citations
4
Citations
Journal
Synlett
Abstract
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.