Stereoselective Synthesis Axially Chiral Arylnitriles through Base-Induced Chirality-Relay β-Carbon Elimination of α-Hydroxyl Ketoxime Esters.

Abstract

We report herein a point-to-axial chirality transfer reaction of α-hydroxyl oxime esters for the synthesis of axially chiral arylnitriles. The reaction proceeds smoothly through a base-promoted retro-benzoin condensation reaction of α-hydroxyl oxime esters, where the axial chirality is created via the C-C bond cleavage based on a proper distorted conformation of the biaryl structure induced by its stereogenic carbon center.