Catalytic intermolecular aldol reactions of transient amide enolates in domino Michael/aldol reactions of nitroalkanes, acrylamides, and aldehydes

Three-component reactions of nitroalkanes, acrylamides, and aldehydes by using a catalytic amount of KOH in DMSO gave β′-hydroxy-γ-nitro amides. Mechanistic studies suggested that the reactions proceeded by domino Michael/aldol reactions. The highly nucleophilic nature of transient amide enolates th...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2021-01, Vol.23 (3), p.116-1164
Main Authors: Morita, Shunya, Yoshimura, Tomoyuki, Matsuo, Jun-ichi
Format: Article
Language:English
Subjects:
Aldehydes
Amides
Anions
Cascade chemical reactions
Crystallography
Green chemistry
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Summary:Three-component reactions of nitroalkanes, acrylamides, and aldehydes by using a catalytic amount of KOH in DMSO gave β′-hydroxy-γ-nitro amides. Mechanistic studies suggested that the reactions proceeded by domino Michael/aldol reactions. The highly nucleophilic nature of transient amide enolates that were formed by Michael addition of nitronate anions to acrylamides in DMSO enabled the realization of catalytic intermolecular aldol reactions of amide enolates in the presence of acidic nitroalkanes. Aldol reactions of amide enolates formed by addition of nitronates to acrylamides proceeded with catalytic amounts of KOH in DMSO.
ISSN:1463-9262
1463-9270
DOI:10.1039/d0gc04111d