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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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Publication details

The article was received on 21 Nov 2010, accepted on 05 Jan 2011 and first published on 06 Jan 2011


Article type: Paper
DOI: 10.1039/C0OB01059F
Org. Biomol. Chem., 2011,9, 2777-2783

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    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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