Engineered non-covalent π interactions as key elements for chiral recognition

Ming Yu Jin, Qianqian Zhen, Dengmengfei Xiao, Guanyu Tao, Xiangyou Xing, Peiyuan Yu () and Chen Xu ()
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Ming Yu Jin: Southern University of Science and Technology
Qianqian Zhen: Southern University of Science and Technology
Dengmengfei Xiao: Southern University of Science and Technology
Guanyu Tao: Southern University of Science and Technology
Xiangyou Xing: Southern University of Science and Technology
Peiyuan Yu: Southern University of Science and Technology
Chen Xu: Southern University of Science and Technology

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Molecular recognition and self-assembly are often mediated by intermolecular forces involving aromatic π-systems. Despite the ubiquity of such interactions in biological systems and in the design of functional materials, the elusive nature of aromatic π interaction results in that they have been seldom used as a design element for promoting challenging chemical reactions. Described here is a well-engineered catalytic system into which non-covalent π interactions are directly incorporated. Enabled by a lone pair-π interaction and a π-π stacking interaction operating collectively, efficient chiral recognition is successfully achieved in the long-pursued dihydroxylation-based kinetic resolution. Density functional theory calculations shed light on the crucial role played by the lone pair-π interaction between the carbonyl oxygen of the cinchona alkaloid ligand and the electron-deficient phthalazine π moiety of the substrate in the stereoselectivity-determining transition states. This discovery serves as a proof-of-principle example showing how the weak non-covalent π interactions, if ingeniously designed, could be a powerful guide in attaining highly enantioselective catalysis.

Date: 2022
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DOI: 10.1038/s41467-022-31026-8

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