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

Keywords

  • Camphor
  • Linker
  • Michael addition
  • Nitroolefins
  • Organocatalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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