Chemical Communications
05 Apr 2022
Facile access to chiral chromanone-2-carboxylic acids enabled by rhodium-catalyzed chemo- and enantioselective hydrogenation
Zhuang Nie,‡ab Song Liu,‡c Tonglin Wang,b Zhanhong Shen,b Huifang Nie,b Jiayue Xi,b Dongxu Zhang,b Xiaohui Zheng,*a Shengyong Zhang*b and Lin Yao*b
a Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, The College of Life Science, Northwest University, Xi'an 710069, P. R. China
b Department of Medicinal Chemistry and Pharmaceutical Analysis, School of Pharmacy, Fourth Military Medical University, Xi'an, 710032, P. R. China
c Chongqing Key Laboratory of Environmental Materials and Remediation Technologies, Chongqing University of Arts and Sciences, Chongqing, 402160, P. R. China
‡ These authors contributed equally to this work.
10.1039/D2CC00589A
Rh-catalyzed highly chemo- and enantioselective hydrogenation of chromone-2-carboxylic acids was successfully established for the first time, providing a wide range of enantiopure chromanone-2-carboxylic acids with excellent results (up to 97% yield and 99% ee) and high efficiency (up to 10 000 TON). The carboxylic group in the substrate was demonstrated to play a vital role and an enantio-induction mode was elucidated by DFT calculation. This hydrogenation protocol provided straightforward access to various bioactive chromanoids.
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