期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 2, 页码 823-828出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo402570t
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资金
- CSIR
- CSIR [BSC0104i]
- DST
The reaction between readily accessible propargyl acetates and sulfonyl azides in the presence of CuI catalyst yields trans-alpha,beta-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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