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Synthesis of axially chiral biaryl-2-carboxamides through Pd(II)-catalyzed atroposelective C–H olefination
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2024-05-13 , DOI: 10.1039/d4qo00493k
Bo-Yang Jiang 1 , Gang Zhou 1 , Ao-Lian Jiang 2 , Tao Zhou 1, 3 , Bing-Feng Shi 1, 3
Affiliation  

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.

中文翻译:


通过 Pd(II) 催化的间质选择性 C-H 烯化合成轴向手性联芳基-2-甲酰胺



在此,我们开发了一种 Pd(II) 催化的酰胺定向的原子选择性 C-H 烯化反应,用于合成具有 N,N-二取代酰胺基团的轴向手性联芳基化合物。使用廉价的市售 (L)-焦谷氨酸 (L-pGlu-OH) 作为手性配体,以良好至优异的产率和对映选择性(高达 96% 产率和 99% ee)获得了多种轴向手性联芳基化合物。值得注意的是,烯化产物可以很容易地转化为具有N,N-二取代酰胺基团的手性羧酸,其可以用作不对称C-H官能化中的羧酸配体。
更新日期:2024-05-13
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