Two different dynamic kinetic resolution methods have been applied for the asymmetric synthesis of pharmaceutical arylpropionic acids and aryloxy acids by using amides of (S)-lactic acid as chiral auxiliaries. For arylpropionic acids the esterification mediated by dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP) proceeds with good asymmetric induction, while for aryloxyacetic acids the keystep is a diastereoselective substitution reaction in the presence of triethylamine and n-hexylammonium iodide as additives.

Asymmetric Synthesis of Arylpropionic Acids and Aryloxy Acids by Using Lactamides as Chiral Auxiliaries

AMMAZZALORSO, Alessandra;AMOROSO, Rosa;BETTONI, Giancarlo;DE FILIPPIS, Barbara;FANTACUZZI, MARIALUIGIA;GIAMPIETRO, Letizia;MACCALLINI, Cristina;TRICCA, Maria Luisa
2006-01-01

Abstract

Two different dynamic kinetic resolution methods have been applied for the asymmetric synthesis of pharmaceutical arylpropionic acids and aryloxy acids by using amides of (S)-lactic acid as chiral auxiliaries. For arylpropionic acids the esterification mediated by dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP) proceeds with good asymmetric induction, while for aryloxyacetic acids the keystep is a diastereoselective substitution reaction in the presence of triethylamine and n-hexylammonium iodide as additives.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11564/134554
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