Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes.

Org Biomol Chem

Laboratorio de Síntesis Asimétrica, Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-CSIC, E-50009, Zaragoza, Aragón, Spain.

Published: April 2011

Bifunctional thiourea catalyzes the enantioselective Michael addition reaction of diphenyl phosphite to nitroalkenes. This methodology provides a facile access to enantiomerically enriched β-nitrophosphonates, precursors for the preparation of synthetically and biologically useful β-aminophosphonic acids. DFT level of computational calculations invoke the attack of the diphenyl phosphite to the nitroolefin by the Re face, this give light to this scarcely explored process update in the literature. The computational calculations support the absolute configuration obtained in the final adducts.

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Source
http://dx.doi.org/10.1039/c0ob01059fDOI Listing

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