Catalytic asymmetric constructions of nitrogen, boron and carbon continuous stereogenic centers

Guan Zhang, Junyi Jia, Xuzhao Du, Bofan Feng, Kai Yang, Peiyuan Yu and Qiuling Song ()
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Guan Zhang: Fujian Normal University
Junyi Jia: College of Chemistry at Fuzhou University
Xuzhao Du: Southern University of Science and Technology Shenzhen
Bofan Feng: College of Chemistry at Fuzhou University
Kai Yang: College of Chemistry at Fuzhou University
Peiyuan Yu: Southern University of Science and Technology Shenzhen
Qiuling Song: College of Chemistry at Fuzhou University

Nature Communications, 2025, vol. 16, issue 1, 1-10

Abstract: Abstract Precise construction of molecular chirality is a longstanding scientific challenge in synthetic chemistry. Although methods to enantioselectively assemble consecutive carbon stereocenters are abundant, courses to establish enriched continuous heteroatomic stereocenters have acquired less attention and remain a tremendous challenge. Of those atoms in main group elements, nitrogen and boron are the most intractable ones to control their chirality. The copper-catalyzed asymmetric insertion reaction is one of the most significant transformations to construct C-B bonds in organic synthesis. Herein, we report a protocol to synthesize troublesome continuous heteroatomic stereocenters from cyclic amine boranes and diazo compounds via asymmetric B-H insertion reaction. The protocol is compatible with a wide range of amine boranes and diazo compounds, exhibiting high diastereo- and enantioselectivities. Mechanistic studies reveal a meaningful kinetic resolution pathway involved in the transformation and DFT calculations elucidate the origins of stereoselectivity and diastereoselectivity.

Date: 2025
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DOI: 10.1038/s41467-025-64905-x

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