Synthesis of axially chiral biaryl-2-carboxamides through Pd(ii)-catalyzed atroposelective C–H olefination

Abstract

Herein, we developed a Pd(II)-catalyzed amide-directed atroposelective C–H olefination for the synthesis of axially chiral biaryls with N,N-disubstituted amide groups. A broad range of axially chiral biaryls were obtained in good to excellent yields and enantioselectivities (up to 96% yield and 99% ee) using inexpensive commercially available (l)-pyroglutamic acid (L-pGlu-OH) as a chiral ligand. Notably, olefination products could be easily transformed to chiral carboxylic acids with N,N-disubstituted amide groups, which could be used as carboxylic acid ligands in asymmetrical C–H functionalizations.