Optically pure γ-butyrolactones and epoxy estersvia two stereocentered HKR of 3-substituted epoxy esters: a formal synthesis of (−)-paroxetine, Ro 67-8867 and (+)-eldanolide

Abstract

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(III)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (−)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.