title: Synthesis of (-)-paroxetine via enantioselective phase-transfer catalytic monoalkylation of malonamide ester.
abstract: A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.
authors.affiliation: Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
authors.forename: Mi-Hyun
authors.initials: MH
authors.lastname: Kim
authors.forename: Yohan
authors.initials: Y
authors.lastname: Park
authors.forename: Byeong-Seon
authors.initials: BS
authors.lastname: Jeong
authors.forename: Hyeung-Geun
authors.initials: HG
authors.lastname: Park
authors.forename: Sang-Sup
authors.initials: SS
authors.lastname: Jew
mesh_terms: D000478:Alkylation; D002384:Catalysis; D004952:Esters; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D008314:Malonates; D017374:Paroxetine; C008314:malonamide