Asymmetric synthesis of arylpropionic acids and aryloxy acids by using lactamides as chiral auxiliaries

被引：20

作者：

Ammazzalorso, Alessandra ^{[1
]}

Amoroso, Rosa ^{[1
]}

Bettoni, Giancarlo ^{[1
]}

De Filippis, Barbara ^{[1
]}

Fantacuzzi, Marialuigia ^{[1
]}

Giampietro, Letizia ^{[1
]}

Maccallini, Cristina ^{[1
]}

Tricca, Maria L. ^{[1
]}

机构：

[1] Univ Studi G DAnnunzio, Dipartimento Scu Farmaco, I-66100 Chieti, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 18期

关键词：

aryloxy acids; arylpropionic acids; dynamic kinetic resolution; chiral auxiliaries; asymmetric synthesis;

D O I：

10.1002/ejoc.200600484

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 key-step is a diastereoselective substitution reaction in the presence of triethylamine and n-hexylammonium iodide as additives. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

引用

页码：4088 / 4091

页数：4

共 22 条

[1] Dynamic kinetic resolution of α-bromoesters containing lactamides as chiral auxiliaries [J].