Cinchona based squaramide catalysed enantioselective Michael addition of a-nitrophosphonates to aryl acrylates: enantioselective synthesis of quaternary a-aminophosphonates

Pham, Truong Son and Gönczi, Katalin and Kardos, György and Süle, Krisztina and Hegedűs, László and Kállay, Mihály and Kubinyi, Miklós and Szabó, Pál and Petneházy, Imre and Tőke, László and Jászay, Zsuzsa (2013) Cinchona based squaramide catalysed enantioselective Michael addition of a-nitrophosphonates to aryl acrylates: enantioselective synthesis of quaternary a-aminophosphonates. Tetrahedron: Asymmetry, 24 (24). pp. 1605-1614. ISSN 0957-4166

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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.

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