Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes

Abstract

7 páginas, 5 figuras, 4 tablas, 1 esquema.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.We thank the Ministry of Science and Innovation (MICINN, Madrid, Spain. Projects CTQ2009-09028 and CTQ2010-19606) and the Government of Aragón (Zaragoza, Spain. Project PI064/09 and Research Groups, E-10) for financial support of our research. E. M.-L. thanks the Alexander von Humboldt Foundation for a postdoctoral fellowship and CSIC for a JAE-Doc contract.Peer reviewe