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