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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.

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  • 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.


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.

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