DOI
doi:10.1016/j.tetlet.2012.08.054
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 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.
Document Type
Post-print Article
Publication Date
10-24-2012
Publisher Statement
Copyright © 2012, Elsevier. The definitive version is available at: http://www.journals.elsevier.com/tetrahedron-letters.
DOI: 10.1016/j.tetlet.2012.08.054
Full Citation:
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.
Recommended Citation
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.
https://scholarship.richmond.edu/chemistry-faculty-publications/17