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Cu-Catalyzed Conversion of Propargyl Acetates to E-α,β-Unsaturated Amides via Ketenimine Formation with Sulfonyl Azides

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† Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India
‡ Academy of Scientific and Innovative Research, New Delhi 110001, India
*E-mail: [email protected], [email protected]
Cite this: J. Org. Chem. 2014, 79, 2, 823–828
Publication Date (Web):December 17, 2013
https://doi.org/10.1021/jo402570t
Copyright © 2013 American Chemical Society
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    Abstract

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    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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    1H and 13C NMR and mass spectra for the products 3a–w. This material is available free of charge via the Internet at http://pubs.acs.org.

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    31. Yalla Kiran Kumar, Gadi Ranjith Kumar, Maddi Sridhar Reddy. ChemInform Abstract: Cu-Catalyzed Conversion of Propargyl Acetates to E-α,β-Unsaturated Amides via Ketenimine Formation with Sulfonyl Azides.. ChemInform 2014, 45 (25) , no-no. https://doi.org/10.1002/chin.201425064
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