Synthesis of axially chiral biaryl-2-carboxamides through Pd(ii)-catalyzed atroposelective C–H olefination†
Tao
Zhou 
*ab
and
Bing-Feng
Shi
*ab
*ab
and
Bing-Feng
Shi
*ab
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.
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