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

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• 作者：Yalla Kiran Kumar ; Gadi Ranjith Kumar ; Maddi Sridhar Reddy
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：January 17, 2014
• 年：2014
• 卷：79
• 期：2
• 页码：823-828
• 全文大小：319K
• ISSN：1520-6904

文摘

The reaction between readily accessible propargyl acetates and sulfonyl azides in the presence of CuI catalyst yields trans-伪,尾-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.