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

58 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

Fingerprint

Bearings (structural)
Camphor
Benzoic Acid
Benzoic acid
Enantioselectivity
Aldehydes
Carbon
Derivatives
Catalysts
pyrrolidine

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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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).",
keywords = "Asymmetric catalysis, Michael reaction, Quaternary carbon centers, Solventfree reaction, β-nitroalkenes",
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T1 - Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes

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AU - Chang, Chihliang

AU - Li, Ssu Hsien

AU - Reddy, Raju Jannapu

AU - Chen, Kwunmin

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N2 - 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).

AB - 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).

KW - Asymmetric catalysis

KW - Michael reaction

KW - Quaternary carbon centers

KW - Solventfree reaction

KW - β-nitroalkenes

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