Pd-Catalyzed Atroposelective C-H Acyloxylation Enabling Access to an Axially Chiral Biaryl Phenol Organocatalyst

Herein, we present the Pd(II)-catalyzed atroposelective C-H acyloxylation strategy for the assembly of biaryl aldehyde atropoisomers using readily available amino acids as the catalytic auxiliary and chiral pool. This strategy exhibits a broad substrate scope with a good yield (<= 90%) and excellent enantioselectivity (<= 99%), furnishing functionalized aldehydes through direct asymmetric C-H oxidation. The application utility of this method was demonstrated by the concise synthesis of a kind of atropoisomeric amino-phenol organocatalyst, which enables good enantiocontrol in catalyzing asymmetric addition of diethylzinc to aldehydes.

Automated summary

In this study, a Pd(II)-catalyzed atroposelective C-H acyloxylation strategy was developed for the synthesis of biaryl aldehyde atropoisomers. Amino acids were used as the catalytic auxiliary and chiral pool. This strategy demonstrates a broad substrate scope, high yield (<= 90%), and excellent enantioselectivity (<= 99%), providing functionalized aldehydes through direct asymmetric C-H oxidation.