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

Zhang, Guan1; Zhang, Zhihan2,3; Hou, Mengyuan1; Cai, Xinping1; Yang, Kai1; Yu, Peiyuan2,3; Song, Qiuling1,2,3,4,5

2022-05-12

10.1038/s41467-022-30287-7

NATURE COMMUNICATIONS   影响因子和分区

2041-1723

["Enantioselective catalytic methods for the construction of boron-stereogenic compounds are elusive. In this article, the authors describe a route to these compounds via a copper-catalysed desymmetric B-H insertion on 2-arylpyridine-boranes with carbenes.","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."]

SCI

英语

NI论文

通讯

National Natural Science Foundation of China[21931013] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Science & Technology - Other Topics

Multidisciplinary Sciences

WOS:000795171100002

NATURE PORTFOLIO

2-s2.0-85130022467

Web of Science

1.Fuzhou Univ, Fujian Prov Univ, Key Lab Mol Synth & Funct Discovery, Coll Chem, Fuzhou 350108, Fujian, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China
4.Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, 668 Jimei Blvd, Xiamen 361021, Fujian, Peoples R China
5.Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

Zhang, Guan,Zhang, Zhihan,Hou, Mengyuan,et al. Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B-H bond insertion reaction[J]. NATURE COMMUNICATIONS,2022,13(1).

Zhang, Guan.,Zhang, Zhihan.,Hou, Mengyuan.,Cai, Xinping.,Yang, Kai.,...&Song, Qiuling.(2022).Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B-H bond insertion reaction.NATURE COMMUNICATIONS,13(1).

Zhang, Guan,et al."Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B-H bond insertion reaction".NATURE COMMUNICATIONS 13.1(2022).