One-pot three-step thioconjugate addition-oxidation-Diels–Alder reactions of ethyl propiolate

CW Downey, S Craciun, CA Vivelo, AM Neferu…

Index: Downey, C. Wade; Craciun, Smaranda; Vivelo, Christina A.; Neferu, Ana M.; Mueller, Carly J.; Corsi, Stephanie Tetrahedron Letters, 2012 , vol. 53, # 43 p. 5766 - 5768

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Citation Number: 6

Abstract

Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta- chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic ...