Development of Axially Chiral Styrene-Type Carboxylic Acid Ligands via Palladium-Catalyzed Asymmetric C-H Alkynylation

A weakly coordinated carboxylate-directed palladium-catalyzed atroposelective C-H alkynylation method for the development of novel axially chiral styrene-type carboxylic acids is disclosed. This transformation exhibits good yields (up to 85%), excellent enantiocontrol (up to 99% ee), and mild conditions. Notably, the synthetic utility of the resulting alkynyl carboxylic acid derivatives was demonstrated by various derivatizations as well as their potential as chiral ligands in asymmetric C-H activations.

Automated summary

A carboxylate-directed palladium-catalyzed atroposelective C-H alkynylation method was developed with good yields and excellent enantioselectivity. The resulting alkynyl carboxylic acid derivatives showed synthetic utility through various derivatizations, as well as potential as chiral ligands in asymmetric C-H activations.