1519103-08-2Relevant academic research and scientific papers
Cu-catalyzed conversion of propargyl acetates to e-a,β-unsaturated amides via ketenimine formation with sulfonyl azides
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Maddi Sridhar
, p. 823 - 828 (2014/04/03)
The reaction between readily accessible propargyl acetates and sulfonyl azides in the presence of CuI catalyst yields trans-a,β-unsaturated Ntosylamides 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 (electrondonating, -withdrawing, and -neutral), heteroaryl, and vinyl groups, on the Cterminal of acrylamide. Also, the method affords the products at ambient temperature with excellent diastereoselectivity in moderate to good yields.
