Amidation of Enones via Beckmann Rearrangement

The Beckmann reaction is one of the most atom-economical methods for the preparation of amides from ketones. Unlike ketones, the multiple competing reactivities of enones as well as the requirement of demanding reaction conditions for in situ generation of oximes have severely impacted the applicati...

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Published inJournal of organic chemistry Vol. 89; no. 11; pp. 8201 - 8207
Main Authors Verma, Saumya, Singh, Vikram, Jat, Jawahar L., Tiwari, Bhoopendra
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
CINNAMIC ACID-DERIVATIVES
DIRECT TRANSFORMATION
AMINES
BOND FORMATION
ALPHA,BETA-UNSATURATED AMIDES
TANDEM REACTION
ACRYLAMIDES
EFFICIENT
MICHAEL ADDITION
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Summary:The Beckmann reaction is one of the most atom-economical methods for the preparation of amides from ketones. Unlike ketones, the multiple competing reactivities of enones as well as the requirement of demanding reaction conditions for in situ generation of oximes have severely impacted the application of this reaction for the preparation of α,β-unsaturated amides. Herein, we describe the first chemoselective method for the direct conversion of enones to the corresponding α,β-unsaturated amides using N-Boc-O-tosylhydroxylamine.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02478