Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions

Chihliang Chang, Ssu Hsien Li, Raju Jannapu Reddy, Kwunmin Chen

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

A novel pyrrolidine-camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α-disubstituted aldehydes with β-nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent-free conditions provided the desired Michael product possessing an all-carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee).

Original languageEnglish
Pages (from-to)1273-1278
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number9
DOIs
Publication statusPublished - 2009 Jun 1

Keywords

  • Asymmetric catalysis
  • Michael reaction
  • Quaternary carbon centers
  • Solventfree reaction
  • β-nitroalkenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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