Thiourea Catalyzed Organocatalytic Enantioselective Michael Addition of Diphenyl Phosphite to Nitroalkenes

Ana Alcaine, Eugenia Marqués-López, Pedro Merino, Tomás Tejero, Raquel P. Herrera . Thiourea Catalyzed Organocatalytic Enantioselective Michael Addition of Diphenyl Phosphite to Nitroalkenes. Org. Biomol. Chem.. 2011, Vol. 9, p. 2777-2011.

Bifunctional thiourea catalyzes the enantioselective Michael addition reaction of diphenyl phosphite to nitroalkenes. This methodology provides a facile access to enantiomerically enriched alfa-nitrophosphonates, precursors for the preparation of synthetically and biologically useful alfa-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