Pyrrolidine-linker-camphor assembly: Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions

Shaik Anwar, Pei Hsun Lee, Tsai Yung Chou, Chihliang Chang, Kwunmin Chen

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A simple and convenient strategy was developed to synthesize a new class of pyrrolidinyl-camphor based bifunctional organocatalysts possessing varying functional linkers. Catalytic screening of these camphor-pyrrolidine linked derivatives for asymmetric Michael reaction of cyclohexanone with β-nitrostyrene was carried out. Various aryl- and heteroaryl-nitroolefins, ketones as well as aldehydes gave the corresponding Michael adducts in high chemical yields (up to 95%) and exceptionally high diastereo-(syn/anti up to 99:1) and enantioselectivity (up to 95%) using catalyst 6 under solvent-free conditions.

Original languageEnglish
Pages (from-to)1171-1177
Number of pages7
JournalTetrahedron
Volume67
Issue number6
DOIs
Publication statusPublished - 2011 Feb 11

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Camphor
Enantioselectivity
Ketones
Aldehydes
Screening
Derivatives
Catalysts
cyclohexanone
pyrrolidine

Keywords

  • Camphor
  • Linker
  • Michael addition
  • Nitroolefins
  • Organocatalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Pyrrolidine-linker-camphor assembly : Bifunctional organocatalysts for efficient Michael addition of cyclohexanone to nitroolefins under neat conditions. / Anwar, Shaik; Lee, Pei Hsun; Chou, Tsai Yung; Chang, Chihliang; Chen, Kwunmin.

In: Tetrahedron, Vol. 67, No. 6, 11.02.2011, p. 1171-1177.

Research output: Contribution to journalArticle

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