Synthesis of dehydro-beta-amino esters via highly regioselective amination of allylic carbonates.
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.
Benfatti
Fides
F
Department of Chemistry G Ciamician, University of Bologna, Bologna, Italy.
Cardillo
Giuliana
G
Gentilucci
Luca
L
Mosconi
Elisa
E
Tolomelli
Alessandra
A
D000085:Acetates / Q000737:chemistry; D000586:Amination; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D002254:Carbonates; D004952:Esters; D010165:Palladium