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Paper | Regular issue | Vol 65, No. 11, 2005, pp.2635-2647
Published online, 19th August, 2005
DOI: 10.3987/COM-05-10494
Stereocontrolled Synthesis of New Tetrahydrofuro[2,3-d]thiazole Derivatives via Activated Vinylogous Iminium Ions

Rade Markovic,* Marija Baranac, Peter Steel, Erich Kleinpeter, and Milovan Stojanovic

*Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O.Box 158, 11001 Belgrade, Serbia and Montenegro

Abstract

Heterocyclization of (Z)-5-(2-hydroxyethyl)-3-methyl-4-oxothiazo-lidines, bearing electron-withdrawing groups conjugated to an exocyclic double bond at C(2)-position, afforded under reductive conditions, cis-tetrahydro-furo[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.