Issue 39, 2022

Facile access to chiral chromanone-2-carboxylic acids enabled by rhodium-catalyzed chemo- and enantioselective hydrogenation

Abstract

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.

Graphical abstract: Facile access to chiral chromanone-2-carboxylic acids enabled by rhodium-catalyzed chemo- and enantioselective hydrogenation

Supplementary files

Article information

Article type
Communication
Submitted
28 Jan 2022
Accepted
04 Apr 2022
First published
05 Apr 2022

Chem. Commun., 2022,58, 5837-5840

Facile access to chiral chromanone-2-carboxylic acids enabled by rhodium-catalyzed chemo- and enantioselective hydrogenation

Z. Nie, S. Liu, T. Wang, Z. Shen, H. Nie, J. Xi, D. Zhang, X. Zheng, S. Zhang and L. Yao, Chem. Commun., 2022, 58, 5837 DOI: 10.1039/D2CC00589A

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