The synthesis of alpha-benzylamino-beta,gamma-unsaturated acids has been developed starting from a-bromo-a,b-unsaturated chlorides. Via treatment of the acyl chlorides with (R)-pantolactone in the presence of TEA, the in situ formation of the deconjugated ketenes and their direct transformation into chiral esters was performed. The substitution of bromine with benzylamine, followed by acid hydrolysis, allowed to us obtain enantiomerically enriched a-benzylamino-b,c-unsaturated acids.
CARDILLO G., S. FABBRONI, L. GENTILUCCI, R. PERCIACCANTE, A. TOLOMELLI (2004). alpha-Bromo-beta,gamma-unsaturated Ketenes as Valuable Intermediates in the Synthesis of alpha-Amino-beta,gamma-Unsaturated Acids. TETRAHEDRON-ASYMMETRY, 15, 593-601.
alpha-Bromo-beta,gamma-unsaturated Ketenes as Valuable Intermediates in the Synthesis of alpha-Amino-beta,gamma-Unsaturated Acids
CARDILLO, GIULIANA;FABBRONI, SERENA;GENTILUCCI, LUCA;PERCIACCANTE, ROSSANA;TOLOMELLI, ALESSANDRA
2004
Abstract
The synthesis of alpha-benzylamino-beta,gamma-unsaturated acids has been developed starting from a-bromo-a,b-unsaturated chlorides. Via treatment of the acyl chlorides with (R)-pantolactone in the presence of TEA, the in situ formation of the deconjugated ketenes and their direct transformation into chiral esters was performed. The substitution of bromine with benzylamine, followed by acid hydrolysis, allowed to us obtain enantiomerically enriched a-benzylamino-b,c-unsaturated acids.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
