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

Ammazzalorso Alessandra | Zendy; Amoroso Rosa | Zendy; Bettoni Giancarlo | Zendy; De Filippis Barbara | Zendy; Fantacuzzi Marialuigia | Zendy; Giampietro Letizia | Zendy; Maccallini Cristina | Zendy; Tricca Maria L. | Zendy

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

Author(s) -

Ammazzalorso Alessandra,

Amoroso Rosa,

Bettoni Giancarlo,

De Filippis Barbara,

Fantacuzzi Marialuigia,

Giampietro Letizia,

Maccallini Cristina,

Tricca Maria L.

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200600484

Subject(s) - chemistry , triethylamine , enantioselective synthesis , kinetic resolution , organic chemistry , pyridine , iodide , catalysis

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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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