Desymmetric Hydrogenation of meso-Dicarboxylic Acids

Yang, Lei1,2; Yang, Tilong3; Qian, Yu1; Zhang, Xumu1; Wen, Jialin4

2024-05-29

10.1021/jacs.4c02538

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   影响因子和分区

0002-7863

1520-5126

Efficient transformation of platform chemicals into key intermediates has been increasingly important for the pharmaceutical industry. The development of the catalytic reduction of abundant carboxylic acids with molecular hydrogen has been of both practical and theoretical value. We herein report the homogeneous hydrogenation of dicarboxylic acids with the strategy of desymmetrization. Using a rhodium/bisphosphine catalyst, one carboxyl group of meso-diacids was selectively reduced to yield chiral lactones with satisfactory enantioselectivity. This method provides a straightforward approach to produce chiral lactone intermediates for the manufacture of biotin, telaprevir, and other antivirus drugs. Both experimental and computational investigations were carried out, revealing a novel neighboring group coordination mechanism in the catalytic cycle.

SCI ; EI

英语

第一 ; 通讯

Chemistry

Chemistry, Multidisciplinary

WOS:001235209400001

AMER CHEMICAL SOC

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
2.Univ Michigan, Dept Med Chem, Ann Arbor, MI 48109 USA
3.Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong 999077, Peoples R China
4.Jiangsu Hengrui Pharmaceut Co Ltd, Lianyungang Inst Res, Dept Chem Proc R&D, Lianyungang 222000, Peoples R China

Yang, Lei,Yang, Tilong,Qian, Yu,et al. Desymmetric Hydrogenation of meso-Dicarboxylic Acids[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2024,146(23).

Yang, Lei,Yang, Tilong,Qian, Yu,Zhang, Xumu,&Wen, Jialin.(2024).Desymmetric Hydrogenation of meso-Dicarboxylic Acids.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,146(23).

Yang, Lei,et al."Desymmetric Hydrogenation of meso-Dicarboxylic Acids".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146.23(2024).