BINOL-based azacrown ether catalyzed enantioselective Michael addition: Asymmetric synthesis of α-aminophosphonates

Truong Son Pham, János B. Czirok, László Balázs, Krisztina Pál, M. Kubinyi, I. Bitter, Zsuzsa Jászay

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Several novel 1,1′-bi-2-naphthyl-appended azacrown ethers with donor side-arms were synthesized and applied for the first time as chiral catalysts in the asymmetric Michael addition of an N-protected aminomethylenephosphonate onto acrylonitriles, resulting in high diastereoselectivity and enantioselectivity. The absolute configuration of the adduct was determined from its experimental and calculated CD spectra.

Original languageEnglish
Pages (from-to)480-486
Number of pages7
JournalTetrahedron Asymmetry
Volume22
Issue number4
DOIs
Publication statusPublished - Feb 24 2011

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Acrylonitrile
Ethers
acrylonitriles
Enantioselectivity
Ether
adducts
ethers
catalysts
Catalysts
synthesis
configurations
naphthol BINOL

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

BINOL-based azacrown ether catalyzed enantioselective Michael addition : Asymmetric synthesis of α-aminophosphonates. / Pham, Truong Son; Czirok, János B.; Balázs, László; Pál, Krisztina; Kubinyi, M.; Bitter, I.; Jászay, Zsuzsa.

In: Tetrahedron Asymmetry, Vol. 22, No. 4, 24.02.2011, p. 480-486.

Research output: Contribution to journalArticle

Pham, Truong Son ; Czirok, János B. ; Balázs, László ; Pál, Krisztina ; Kubinyi, M. ; Bitter, I. ; Jászay, Zsuzsa. / BINOL-based azacrown ether catalyzed enantioselective Michael addition : Asymmetric synthesis of α-aminophosphonates. In: Tetrahedron Asymmetry. 2011 ; Vol. 22, No. 4. pp. 480-486.
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