Cu-Catalyzed Conversion of Propargyl Acetates to E-α,β-Unsaturated Amides via Ketenimine Formation with Sulfonyl Azides
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive InfoField | Value | |
Creator |
Kumar, Y K
Kumar, G R Reddy, M S |
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Date |
2014-05-29T11:40:14Z
2014-05-29T11:40:14Z 2014 |
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Identifier |
J. Org. Chem. 2014, 79, 823−828
http://hdl.handle.net/123456789/1268 |
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Description |
The reaction between readily accessible propargyl acetates and sulfonyl azides in presence of CuI catalyst yielded trans α, β-unsaturated N-tosylamides via N-sulfonyl ketimine formation followed by a probable 1,3-OAc migration ([3,3]-sigmatropic rearrangement). The reaction was very general allowing all kinds of substitution, i.e. alkyl, aryl (electron donating, withdrawing and neutral), heteroaryl and vinyl groups, on the C-terminal of acrylamide. Also, the method afforded the products at ambient temperature with excellent diastereoselectivity and in moderate to good yields.
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186072 bytes
application/pdf |
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Language |
en
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Relation |
CSIR-CDRI Communication No.8589
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Subject |
Cu-Catalyzed
Propargyl Acetates β-Unsaturated Ketenimine Sulfonyl Azides |
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Title |
Cu-Catalyzed Conversion of Propargyl Acetates to E-α,β-Unsaturated Amides via Ketenimine Formation with Sulfonyl Azides
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Type |
Article
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