Stereoselective Synthesis Axially Chiral Arylnitriles through Base-Induced Chirality-Relay β-Carbon Elimination of α-Hydroxyl Ketoxime Esters
Xue Zhang, Xiaoping Xue, Zhenhua Gu
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.
Topics & Concepts
ChemistryStereocenterChirality (physics)Axial chiralityOximeStereoselectivityStereochemistryAxial symmetryAsymmetric carbonEnantioselective synthesisMedicinal chemistryOrganic chemistryCatalysisAlkylChiral symmetryStructural engineeringPhysicsQuarkNambu–Jona-Lasinio modelQuantum mechanicsEngineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis