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Issue 8, 2011
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Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes

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Abstract

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.

Graphical abstract: Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes

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Article information


Submitted
21 Nov 2010
Accepted
05 Jan 2011
First published
06 Jan 2011

Org. Biomol. Chem., 2011,9, 2777-2783
Article type
Paper

Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes

A. Alcaine, E. Marqués-López, P. Merino, T. Tejero and R. P. Herrera, Org. Biomol. Chem., 2011, 9, 2777
DOI: 10.1039/C0OB01059F

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