1450899-78-1Relevant articles and documents
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
Zhai, Jiao-Jiao,Jiang, Jian-An,Zhang, Shun-Li,Chen, Cheng,Liu, Hong-Wei,Liao, Dao-Hua,Ji, Ya-Fei
supporting information, p. 1399 - 1404 (2013/07/26)
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. Georg Thieme Verlag Stuttgart · New York.