Stereocontrolled synthesis of new tetrahydrofuro[2,3-d]thiazole derivatives via activated vinylogous iminium ions
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Heterocyclization of (Z)-5-(2-hydroxyethyl)-3-methyl-4-oxothiazolidines, bearing electron-withdrawing groups conjugated to an exocyclic double bond at C(2)-position, afforded under reductive conditions, cis-tetrahydroftiro[2,3-d]thiazole derivatives. The reactions of these functionalized push-pull beta-enamines occur in a stereocontrolled fashion via activated vinylogous N-methyliminium ions, which are trapped by an internal hydroxyethyl group.
Source:Heterocycles, 2005, 65, 11, 2635-2647
- Pergamon-Elsevier Science Ltd, Oxford