Novel prolinamide-camphor-containing organocatalysts for direct asymmetric michael addition of unmodified aldehydes to nitroalkenes

Raju Jannapu Reddy, Hsuan Hao Kuan, Tsai Yung Chou, Kwunmin Chen

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

A new prolinamide-derived organocatalysts 4a-c that contain a structural rigid bicyclic camphor scaffold were used for the first time in organocatalysis. The aldehyde was added to a mixture of catalyst 4b and the corresponding nitroalkene in CHCl3/MeOH. The reaction mixture was stirred at either ambient temperature or 0°C. The reaction mixture was subject to flash column chromatography on silica gel to give a pure Michael product. The enantiomeric excess of Michael products was determined by chiral HPLC analysis. The enantiomeric purity was determined by using Chiralcel OD-H. Both catalysts performed poorly in the reaction between propionaldehyde and trans-β-nitrostyrene, indicating that the hydroxyl group in 4b must play some role in determining the stereochemical outcomes of the reaction.

Original languageEnglish
Pages (from-to)9294-9298
Number of pages5
JournalChemistry - A European Journal
Volume15
Issue number37
DOIs
Publication statusPublished - 2009 Sep 21

Fingerprint

Camphor
Silica Gel
Aldehydes
Hydroxyl Radical
Chromatography
High Pressure Liquid Chromatography
Temperature
Column chromatography
Catalysts
Scaffolds
cellulose tris-3,5-dimethylphenyl-carbamate
prolinamide
propionaldehyde

Keywords

  • Asymmetric catalysis
  • Camphor
  • Michael addition
  • Nitroalkenes
  • Organocatalysis
  • Triazoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Novel prolinamide-camphor-containing organocatalysts for direct asymmetric michael addition of unmodified aldehydes to nitroalkenes. / Reddy, Raju Jannapu; Kuan, Hsuan Hao; Chou, Tsai Yung; Chen, Kwunmin.

In: Chemistry - A European Journal, Vol. 15, No. 37, 21.09.2009, p. 9294-9298.

Research output: Contribution to journalArticle

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