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