One-pot synthesis of (Z)-B-sulfonyl enoates from ethyl propiolate

Authors

C. Wade Downey, University of RichmondFollow
Smaranda Craciun
Ana M. Neferu
Christina A. Vivelo
Carly J. Mueller
Brian C. Southall
Stephanie Corsi
Eric W. Etchill
Ryan J. Sault

DOI

doi:10.1016/j.tetlet.2012.08.051

Abstract

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%.

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.2012.08.051

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.

Recommended Citation

Downey, C. Wade; Craciun, Smaranda; Neferu, Ana M.; Vivelo, Christina A.; Mueller, Carly J.; Southall, Brian C.; Corsi, Stephanie; Etchill, Eric W.; and Sault, Ryan J., "One-pot synthesis of (Z)-B-sulfonyl enoates from ethyl propiolate" (2012). Chemistry Faculty Publications. 16.
https://scholarship.richmond.edu/chemistry-faculty-publications/16