title: Cu-catalyzed conversion of propargyl acetates to E-α,β-unsaturated amides via ketenimine formation with sulfonyl azides.
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.
authors.affiliation: 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.
authors.forename: Yalla Kiran
authors.initials: YK
authors.lastname: Kumar
authors.forename: Gadi
authors.initials: G
authors.lastname: Ranjith Kumar
authors.forename: Maddi Sridhar
authors.initials: MS
authors.lastname: Reddy
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000085:Acetates; D000480:Alkynes; D000577:Amides; D001386:Azides; D007659:Ketones; D003300:Copper