Format

Send to

Choose Destination
See comment in PubMed Commons below
J Org Chem. 2014 Jan 17;79(2):823-8. doi: 10.1021/jo402570t. Epub 2013 Dec 27.

Cu-catalyzed conversion of propargyl acetates to E-α,β-unsaturated amides via ketenimine formation with sulfonyl azides.

Author information

  • 1Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute , BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India.

Abstract

The reaction between readily accessible propargyl acetates and sulfonyl azides in the presence of CuI catalyst yields trans-α,β-unsaturated N-tosylamides via N-sulfonyl ketenimine formation followed by a probable 1,3-OAc migration ([3,3]-sigmatropic rearrangement). The reaction is very general, allowing all kinds of substitution, including alkyl, aryl (electron-donating, -withdrawing, and -neutral), heteroaryl, and vinyl groups, on the C-terminal of acrylamide. Also, the method affords the products at ambient temperature with excellent diastereoselectivity in moderate to good yields.

[PubMed - indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society
    Loading ...
    Write to the Help Desk