Polarizability matters in enantio-selection

Fumin Chen, Yu Chen, Xiao-Yong Chang, Dongxu He, Qingjing Yang, David Zhigang Wang, Chen Xu (), Peiyuan Yu () and Xiangyou Xing ()
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Fumin Chen: Harbin Institute of Technology
Yu Chen: Southern University of Science and Technology
Xiao-Yong Chang: Southern University of Science and Technology
Dongxu He: Southern University of Science and Technology
Qingjing Yang: Southern University of Science and Technology
David Zhigang Wang: Shenzhen Youwei Tech Group
Chen Xu: Southern University of Science and Technology
Peiyuan Yu: Southern University of Science and Technology
Xiangyou Xing: Southern University of Science and Technology

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract The prevalence of chirality, or, handedness in biological world is a fundamental phenomenon and a characteristic hallmark of life. Thus, understanding the origin of enantio-selection, i.e., the sense and magnitude of asymmetric induction, has been a long-pursued goal in asymmetric catalysis. Herein, we demonstrated a polarizability-derived electronic effect that was shown to be capable of rationalizing a broad range of stereochemical observations made in the field of asymmetric catalysis. This effect provided a consistent enantio-control model for the prediction of major enantiomers formed in a ruthenium-catalyzed asymmetric transfer hydrogenations of ketones. Direct and quantitative linear free energy relationships between substrates’ local polarizabilities and observed enantio-selectivity were also revealed in three widely known asymmetric catalytic systems covering both reductions and oxidations. This broadly applicable polarizability-based electronic effect, in conjunction with conventional wisdom mainly leveraging on steric effect considerations, should aid rational design of enantio-selective processes for better production of chiral substances.

Date: 2024
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DOI: 10.1038/s41467-024-47813-4

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