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

Shunya Morita, Tomoyuki Yoshimura, Jun Ichi Matsuo

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1160-1164
Number of pages5
JournalGreen Chemistry
Volume23
Issue number3
DOIs
Publication statusPublished - 7 Feb 2021

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