B-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from ethyl propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of aliphatic thiols. Addition of meta-chloroperbenzoic acid (mCPBA) and LiClO4 to the reaction mixture provides rapid access to the sulfonyl enoates. Yields of the pure Z isomer range from 51 – 90%.

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Copyright © 2012, Elsevier. The definitive version is available at:

DOI: 10.1016/j.tetlet.2012.08.051

Full Citation:

Downey, C. Wade, Smaranda Craciun, Ana M. Neferu, Christina A. Vivelo, Carly J. Mueller, Brian C. Southall, Stephanie Corsi, Eric W. Etchill, and Ryan J. Sault. "One-pot Synthesis of (Z)-B-sulfonyl Enoates from Ethyl Propiolate."Tetrahedron Letters 53, no. 43 (October 24, 2012): 5763-765. doi:10.1016/j.tetlet.2012.08.051.