Synthesis of (-)-paroxetine via enantioselective phase-transfer catalytic monoalkylation of malonamide ester.
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.
Kim
Mi-Hyun
MH
Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Park
Yohan
Y
Jeong
Byeong-Seon
BS
Park
Hyeung-Geun
HG
Jew
Sang-Sup
SS
D000478:Alkylation; D002384:Catalysis; D004952:Esters; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004952:Esters; D008314:Malonates; D017374:Paroxetine; C008314:malonamide