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 products range from 47 to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step by step.
Copyright © 2012, Elsevier. The definitive version is available at: http://www.journals.elsevier.com/tetrahedron-letters.
Downey, C. Wade, Smaranda Craciun, Christina A. Vivelo, Ana M. Neferu, Carly J. Mueller, and Stephanie Corsi. "One-pot Three-step Thioconjugate Addition-oxidation-Diels–Alder Reactions of Ethyl Propiolate." Tetrahedron Letters 53, no. 43 (October 24, 2012): 5766-768. doi:10.1016/j.tetlet.2012.08.054.
Downey, C. Wade; Craciun, Smaranda; Vivelo, Christina A.; Neferu, Ana M.; Mueller, Carly J.; and Corsi, Stephanie, "One-pot three-step thioconjugate addition-oxidation-Diels–Alder reactions of ethyl propiolate" (2012). Chemistry Faculty Publications. 17.