title: Tandem addition of trialkyl phosphites to alpha,beta-unsaturated imines: a comparison with silylated phosphites.
abstract: Trialkyl phosphites were evaluated for addition reactions to alpha,beta-unsaturated imines. An acidic medium is required to allow consecutive 1,4- and 1,2-addition to occur. In this manner, 3-phosphonyl-1-aminophosphonates, phosphonic acid analogues of glutamate, are obtained in good yields (32-90%). The reaction is mainly influenced by the steric bulk of the nitrogen substituent: less steric N-substituents lead to better yields of the tandem adducts.
authors.affiliation: Research Group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Ellen
authors.initials: E
authors.lastname: Van Meenen
authors.forename: Kristof
authors.initials: K
authors.lastname: Moonen
authors.forename: Annelies
authors.initials: A
authors.lastname: Verwée
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
mesh_terms: D018698:Glutamic Acid / Q000031:analogs & derivatives; D007097:Imines / Q000737:chemistry*; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D063065:Organophosphonates / Q000138:chemical synthesis; D017905:Phosphites / Q000737:chemistry*
chemical_list: D007097:Imines; D063065:Organophosphonates; D017905:Phosphites; D018698:Glutamic Acid; D019158:N-Acetylneuraminic Acid