Construction of C-B axial chirality via dynamic kinetic asymmetric cross-coupling mediated by tetracoordinate boron

Kai Yang, Yanfei Mao, Zhihan Zhang, Jie Xu, Hao Wang, Yong He, Peiyuan Yu () and Qiuling Song ()
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Kai Yang: Fujian Province University, College of Chemistry at Fuzhou University
Yanfei Mao: Fujian Province University, College of Chemistry at Fuzhou University
Zhihan Zhang: Southern University of Science and Technology
Jie Xu: Fujian Province University, College of Chemistry at Fuzhou University
Hao Wang: Fujian Province University, College of Chemistry at Fuzhou University
Yong He: Fujian Province University, College of Chemistry at Fuzhou University
Peiyuan Yu: Southern University of Science and Technology
Qiuling Song: Fujian Province University, College of Chemistry at Fuzhou University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Catalytic dynamic kinetic asymmetric transformation (DyKAT) provides a powerful tool to access chiral stereoisomers from racemic substrates. Such transformation has been widely employed on the construction of central chirality, however, the application in axial chirality remains underexplored because its equilibrium of substrate enantiomers is limited to five-membered metalacyclic intermediate. Here we report a tetracoordinate boron-directed dynamic kinetic asymmetric cross-coupling of racemic, configurationally stable 3-bromo-2,1-azaborines with boronic acid derivatives. A series of challenging C-B axially chiral compounds were prepared with generally good to excellent enantioselectivities. Moreover, this transformation can also be extended to prepare atropisomers bearing adjacent C-B and C-C diaxes with excellent diastereo- and enantio-control. The key to the success relies on the rational design of a reversible tetracoordinate boron intermediate, which is supported by theoretical calculations that dramatically reduces the rotational barrier of the original C-B axis and achieves the goal of DyKAT.

Date: 2023
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DOI: 10.1038/s41467-023-40164-6

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