Diastereoconvergent Synthesis of (-)-Paroxetine

作者：Chamorro Arenas Delfino; Fuentes Lilia; Quintero Leticia; Cruz Gregorio Silvano; Hopfl Herbert; Sartillo Piscil Fernando^*

来源：European Journal of Organic Chemistry, 2017, 2017(28): 4104-4110.

DOI：10.1002/ejoc.201700658

• Nitrogen heterocycles
• Ring opening
• Epoxides
• Total synthesis
• Asymmetric synthesis
• Alkaloids

A diastereoconvergent approach to (-)-paroxetine from diastereomeric 3,4-epoxy-2-piperidones is reported. For this synthesis, a regioselective and stereodivergent Cu-I-catalyzed epoxide-ring-opening reaction of epoxyamide precursors to give the 4-(4-fluorophenyl)-2-piperidone skeleton with the correct absolute configuration is crucial. Using CuBrSMe2 as a catalyst, the epoxide-ring-opening reaction takes place with inversion of configuration; the configuration is retained when CuI is used.

• 出版日期2017-8-2