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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)