Gao Qian, Li Yinwu, Chen Lili, Xie Liang-Jun, Shao Xiangfeng, Ke Zhuofeng, Xu Senmiao
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
J Am Chem Soc. 2025 Jan 8;147(1):88-95. doi: 10.1021/jacs.4c14890. Epub 2024 Dec 18.
Functional group-directed site- and enantioselective C(sp)-H functionalization of alcohols or masked alcohols represents a formidable challenge. We herein report the first example of iridium-catalyzed asymmetric α-C(sp)-H borylation of primary alcohol-derived carbamates by the judicious choice of directing groups. A variety of chiral borylated carbamates were obtained with good to high enantioselectivities. We also demonstrated the synthetic utility by taking advantage of the highly transformable feature of C-B bonds and the leaving ability of carbamates.
醇或掩蔽醇的官能团导向的位点和对映选择性C(sp)-H官能化是一项艰巨的挑战。我们在此报告了通过合理选择导向基团实现铱催化的伯醇衍生氨基甲酸酯的不对称α-C(sp)-H硼化的首例。以良好至高对映选择性获得了多种手性硼化氨基甲酸酯。我们还利用C-B键的高度可转化特性和氨基甲酸酯的离去能力展示了其合成效用。
