A novel synthesis of chiral ibuprofen by a dynamic kinetic resolution process is described. The racemic ibuprofen was converted into the corresponding diastereomeric mixtures of esters with amides of (S)-lactic acid as chiral auxiliaries, using dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as condensation agents. The reactions afforded predominantly one of the two diastereomers with good diastereomeric ratios. The reasons of the stereoselectivity were also investigated by molecular mechanic calculations, using MM2 force fields. (C) 2002 Elsevier Science Ltd. All rights reserved.
Asymmetric synthesis of (S)-ibuprofen by esterification with amides of (S)-lactic acid as chiral auxiliaries: experimental and theoretical results / Alessandra, Ammazzalorso; Rosa, Amoroso; Giancarlo, Bettoni; Barbara De, Filippis; Letizia, Giampietro; Pierini, Marco; Maria Luisa, Tricca. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 43:24(2002), pp. 4325-4328. [10.1016/s0040-4039(02)00792-x]
Asymmetric synthesis of (S)-ibuprofen by esterification with amides of (S)-lactic acid as chiral auxiliaries: experimental and theoretical results
PIERINI, MARCO;
2002
Abstract
A novel synthesis of chiral ibuprofen by a dynamic kinetic resolution process is described. The racemic ibuprofen was converted into the corresponding diastereomeric mixtures of esters with amides of (S)-lactic acid as chiral auxiliaries, using dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) as condensation agents. The reactions afforded predominantly one of the two diastereomers with good diastereomeric ratios. The reasons of the stereoselectivity were also investigated by molecular mechanic calculations, using MM2 force fields. (C) 2002 Elsevier Science Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
