L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones

Dinesh Kumar, Damodara N. Kommi, Pradeep Chopra, Md Imam Ansari, Asit K. Chakraborti*

*Corresponding author for this work

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.

Original languageEnglish
Pages (from-to)6407-6413
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2012
Issue number32
DOIs
Publication statusPublished - Nov 2012
Externally publishedYes

Keywords

  • amino acids
  • domino reactions
  • hydrogen bonds
  • organocatalysis
  • synthetic methods

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