Cinchona based squaramide catalysed enantioselective Michael addition of α-nitrophosphonates to aryl acrylates

Enantioselective synthesis of quaternary α-aminophosphonates

Truong Son Pham, Katalin Gönczi, György Kardos, Krisztina Süle, L. Hegedûs, M. Kállay, M. Kubinyi, P. Szabó, Imre Petneházy, L. Tőke, Zsuzsa Jászay

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Several cinchona based squaramide catalysts were applied to the asymmetric Michael addition of α-nitroethylphosphonates to acrylic acid aryl esters, resulting in high yields and enantioselectivities. The absolute configuration of one of the quaternary α-nitrophosphonate adducts was deduced from its experimental and calculated CD spectra. The adducts were reduced to their cyclic aminophosphonates by catalytic hydrogenation.

Original languageEnglish
Pages (from-to)1605-1614
Number of pages10
JournalTetrahedron Asymmetry
Volume24
Issue number24
DOIs
Publication statusPublished - Dec 31 2013

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Cinchona
Acrylates
Enantioselectivity
acrylates
adducts
Acrylics
Hydrogenation
Esters
Catalysts
Acids
acrylic acid
synthesis
hydrogenation
esters
catalysts
configurations

ASJC Scopus subject areas

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

Cite this

Cinchona based squaramide catalysed enantioselective Michael addition of α-nitrophosphonates to aryl acrylates : Enantioselective synthesis of quaternary α-aminophosphonates. / Pham, Truong Son; Gönczi, Katalin; Kardos, György; Süle, Krisztina; Hegedûs, L.; Kállay, M.; Kubinyi, M.; Szabó, P.; Petneházy, Imre; Tőke, L.; Jászay, Zsuzsa.

In: Tetrahedron Asymmetry, Vol. 24, No. 24, 31.12.2013, p. 1605-1614.

Research output: Contribution to journalArticle

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