Pd-Catalyzed kinetic resolution of benzylic alcohols: a practical synthesis of (R)-tomoxetine and (S)-fluoxetine hydrochlorides

✍ Scribed by Iliyas Sayyed Ali; Arumugam Sudalai

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 73 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01073-0

✦ Synopsis

A convenient synthetic route to (R)-tomoxetine hydrochloride (90% ee) and (S)-fluoxetine hydrochloride (84% ee) is described. (S)-3-Phenyl-3-hydroxypropyl p-toluenesulphonate, the key intermediate, is obtained by the oxidative kinetic resolution of the corresponding racemic 3-phenyl-3-hydroxypropyl p-toluenesulphonate using (-)-sparteine/Pd(II)/O 2 (1 atm) catalytic system.