Literature DB >> 21350778

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

Ana Alcaine1, Eugenia Marqués-López, Pedro Merino, Tomás Tejero, Raquel P Herrera.   

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.

Entities:  

Year:  2011        PMID: 21350778     DOI: 10.1039/c0ob01059f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  1 in total

1.  Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: Beneficial effects of molecular sieves.

Authors:  Santhi Abbaraju; Mayur Bhanushali; Cong-Gui Zhao
Journal:  Tetrahedron       Date:  2011-09-30       Impact factor: 2.457

  1 in total

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