Jiang Ao-Lian, Zhou Gang, Jiang Bo-Yang, Zhou Tao, Xu Xue-Tao, Shi Bing-Feng
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China.
Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
Org Lett. 2024 Jul 12;26(27):5670-5675. doi: 10.1021/acs.orglett.4c01656. Epub 2024 Jun 26.
Axially chiral carboxylic acids are important motifs in chiral catalysts and ligands. We herein reported the synthesis of axially chiral carboxylic acids via Pd(II)-catalyzed atroposelective C-H olefination using carboxylic acid as the native directing group. A broad range of axial chiral biaryl-2-carboxylic acids were synthesized in good yields with high enantioselectivities (up to 84% yield with 99% ee). Gram-scale reaction and further transformation reactions also provide a platform for synthetic applications of this method.
轴手性羧酸是手性催化剂和配体中的重要结构单元。我们在此报道了以羧酸作为天然导向基团，通过钯（II）催化的对映选择性C-H烯基化反应合成轴手性羧酸。一系列轴手性联芳基-2-羧酸以良好的收率和高对映选择性被合成出来（收率高达84%，对映体过量值高达99%）。克级规模反应及进一步的转化反应也为该方法的合成应用提供了一个平台。
