Cu(I)-Catalyzed Synthesis of beta,gamma-Unsaturated Amides

Readily available propargyl alcohols were found to be useful substrates for the copper(I)-catalyzed synthesis of beta,gamma-unsaturated amides. Nucleophilic attack by the alcohol on the in situ generated ketenimine followed by base-catalyzed elimination and subsequent ring opening yields the desired...

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Bibliographic Details
Published inSynlett Vol. 29; no. 4; pp. 463 - 466
Main Authors Bosse, Aaron T., Tsougranis, Gregory H., DeTroia, Christopher D., Tejidor, Francisco J., Isaacs, Andre K.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
SULFONYL AZIDE
amides
propargyl alcohol
CONVERSION
ketenimine
CuAAC
click chemistry
TERMINAL ALKYNES
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Summary:Readily available propargyl alcohols were found to be useful substrates for the copper(I)-catalyzed synthesis of beta,gamma-unsaturated amides. Nucleophilic attack by the alcohol on the in situ generated ketenimine followed by base-catalyzed elimination and subsequent ring opening yields the desired products under mild conditions.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1589135