Stereocontrolled Synthesis of New Tetrahydrofuro[2,3-d]thiazole Derivatives via Activated Vinylogous Iminium Ions (2005)
Intramolecular 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, not easily accessible cis-tetrahydrofuro[2,3-d]thiazole derivatives. The reactions of these functionalized push-pull β-enamines occur in a stereocontrolled fashion via activated vinylogous N-methyliminium ions, which are trapped by an internal hydroxyethyl group.
CitationMarkovic, R., Baranac, M., Steel, P., Kleinpeter, E., Stojanovic, M. (2005) Stereocontrolled Synthesis of New Tetrahydrofuro[2,3-d]thiazole Derivatives via Activated Vinylogous Iminium Ions. Heterocycles, 65, pp. 2635-2647.
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Keywordsthiazolidines; vinylogous N-iminium ion; heterocyclization
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