Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres

Su, Wanlan1; Zhu, Jide1; Chen, Yu2,3; Zhang, Xu1; Qiu, Weihua1; Yang, Kai1; Yu, Peiyuan2,3; Song, Qiuling1

2024-04-01

10.1038/s41557-024-01505-0

NATURE CHEMISTRY   影响因子和分区

1755-4330

1755-4349

["Bioisosteric replacement has emerged as a clear strategy for drug-structure optimization. Naphthalene is the core element of many chiral pharmaceuticals and drug candidates. However, as a promising isostere of naphthalene, the chiral version of 1,2-benzazaborine has rarely been explored due to the lack of efficient synthetic methods. Here we describe a copper-catalysed enantioselective hydroboration of alkenes with 1,2-benzazaborines. The method provides a general platform for the atom-economic and efficient construction of diverse chiral 1,2-benzazaborine compounds (more than 60 examples) that bear a 2-carbon-stereogenic centre or allene skeleton in high yields and excellent enantioselectivities. Three 1,2-benzazaborine analogues of bioactive chiral naphthalene-containing molecules have been prepared, and a series of transformations around chiral 1,2-benzazaborines have also been developed. Notably, the hydroboration process of this study reveals that the identity of 1,2-benzazaborine plays an essential role in the rate-determining step and catalyst resting state.","Chiral 1,2-benzazaborines are promising isosteres of naphthalene, but rarely explored due to the lack of efficient synthetic methods. Now, the copper-catalysed enantioselective hydroboration of alkenes with 1,2-benzazaborines has been developed, providing a general platform for the atom-economic and efficient construction of diverse chiral 1,2-benzazaborine compounds bearing a 2-carbon-stereogenic centre or allene skeleton."]

SCI

英语

通讯

National Natural Science Foundation of China (National Science Foundation of China)["22271048","22001038","21931013","22271105"] ; National Natural Science Foundation of China["2022J05016","2022J02009"] ; Natural Science Foundation of Fujian Province[510578] ; Fuzhou University[2020B121201002] ; Guangdong Provincial Key Laboratory of Catalysis[KQTD20210811090112004]

Chemistry

Chemistry, Multidisciplinary

WOS:001198528600001

NATURE PORTFOLIO

Web of Science

1.Fuzhou Univ, Fujian Prov Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou, Fujian, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Guangdong Prov Key Lab Catalysis, Shenzhen, Peoples R China

Su, Wanlan,Zhu, Jide,Chen, Yu,et al. Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres[J]. NATURE CHEMISTRY,2024.

Su, Wanlan.,Zhu, Jide.,Chen, Yu.,Zhang, Xu.,Qiu, Weihua.,...&Song, Qiuling.(2024).Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres.NATURE CHEMISTRY.

Su, Wanlan,et al."Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres".NATURE CHEMISTRY (2024).