希土類錯体を用いるα，β-不飽和アミドの触媒的不斉エポキシ化反応（2）--位置選択的開環反応を用いた抗うつ薬Fluoxetineの触媒的不斉合成

摘要

We succeeded in obtaining various chiral alpha,beta-epoxy amides by epoxidation of alpha,beta-epoxy unsaturated amides (up to 99 percent yield, >99 percent ee) or imidazolides (up to 91 percent yield, 93 percent ee) using lanthanide-BINOL complexes. alpha,beta-Epoxy amides can be converted into useful chiral building blocks, such as alpha-hydroxy amides and beta-hydroxy amides, but there are no reports on regioselective epoxide opening reaction of alpha,beta-epoxy amides. Herein, we report the new epoxide opening process of alpha,beta-epoxy amides to the corresponding both alpha- and beta-hydroxy amides. These reactions can apply to efficient catalytic asymmetric syntheses of various biologically active compounds.