Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction

Guan Zhang, Zhihan Zhang, Mengyuan Hou, Xinping Cai, Kai Yang, Peiyuan Yu () and Qiuling Song ()
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Guan Zhang: Fujian Province University, College of Chemistry at Fuzhou University
Zhihan Zhang: Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology
Mengyuan Hou: Fujian Province University, College of Chemistry at Fuzhou University
Xinping Cai: Fujian Province University, College of Chemistry at Fuzhou University
Kai Yang: Fujian Province University, College of Chemistry at Fuzhou University
Peiyuan Yu: Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology
Qiuling Song: Fujian Province University, College of Chemistry at Fuzhou University

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: Abstract Compared with the well-developed carbon-stereogenic chemistry, the construction of boron-stereogenic compounds remains undeveloped and challenging. Herein, the previously elusive catalytic enantioselective construction of boron-stereogenic compounds has been achieved through enantioselective desymmetric B–H bond insertion reaction. The B–H bond insertion reaction of 2-arylpyridine-boranes with versatile diazo compounds under chiral copper catalyst can afford boron-stereogenic compounds with good to excellent enantioselectivity. Moreover, the synthetic utility of this reaction is demonstrated by the scalability and downstream transformations. DFT calculations provide insights into the reaction mechanism and the origin of stereoselectivity.

Date: 2022
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DOI: 10.1038/s41467-022-30287-7

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