Tandem addition of trialkyl phosphites to alpha,beta-unsaturated imines: a comparison with silylated phosphites.
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.
Van Meenen
Ellen
E
Research Group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Moonen
Kristof
K
Verwée
Annelies
A
Stevens
Christian V
CV
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*
D007097:Imines; D063065:Organophosphonates; D017905:Phosphites; D018698:Glutamic Acid; D019158:N-Acetylneuraminic Acid