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, László Hegedus, Mihály Kállay, Miklós Kubinyi, Pál Szabó, Imre Petneházy, László Toke, Zsuzsa Jászay

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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

ASJC Scopus subject areas

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

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