Kumar Yalla Kiran, Ranjith Kumar Gadi, Reddy Maddi Sridhar
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.
J Org Chem. 2014 Jan 17;79(2):823-8. doi: 10.1021/jo402570t. Epub 2013 Dec 27.
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.
在碘化亚铜催化剂存在下，易得的炔丙基乙酸酯与磺酰叠氮化物之间的反应通过形成N-磺酰基烯酮亚胺，随后可能发生1,3-乙酸根迁移（[3,3] - 迁移重排）生成反式α,β-不饱和N-甲苯磺酰胺。该反应具有很强的通用性，允许丙烯酰胺C端存在各种取代基，包括烷基、芳基（供电子、吸电子和中性）、杂芳基和乙烯基。此外，该方法在室温下即可得到产物，具有优异的非对映选择性，产率中等至良好。
