title: Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates.
abstract: The allylic amination of acetates and carbonates affords dehydro-beta-aminoesters, which are useful precursors of biologically active compounds. The uncatalyzed reaction proceeds via a S(N)2' mechanism. On the other hand, under palladium-catalyzed conditions, the reaction shows a strong solvent-dependent regiocontrol, affording exclusively one of the two possible regioisomers with complete transfer of chirality from the substrates to the products.
authors.affiliation: Department of Chemistry G Ciamician, University of Bologna, Bologna, Italy.
authors.forename: Fides
authors.initials: F
authors.lastname: Benfatti
authors.forename: Giuliana
authors.initials: G
authors.lastname: Cardillo
authors.forename: Luca
authors.initials: L
authors.lastname: Gentilucci
authors.forename: Elisa
authors.initials: E
authors.lastname: Mosconi
authors.forename: Alessandra
authors.initials: A
authors.lastname: Tolomelli
mesh_terms: D000085:Acetates / Q000737:chemistry; D000586:Amination; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D002254:Carbonates; D004952:Esters; D010165:Palladium