Issue 13, 2024

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
17 Mar 2024
Accepted
10 May 2024
First published
13 May 2024

Org. Chem. Front., 2024,11, 3710-3716

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

B. Jiang, G. Zhou, A. Jiang, T. Zhou and B. Shi, Org. Chem. Front., 2024, 11, 3710 DOI: 10.1039/D4QO00493K

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