通过铑催化硝酮与环状碳酸酯的偶联反应合成桥连环异恶唑啉骨架
Synthesis of Bridged Cycloisoxazoline Scaffolds via Rhodium-Catalyzed Coupling of Nitrones with Cyclic Carbonate.
作者信息
Zhu Man, Zhu Mengdie, Wei Fangjie, Shao Chongjing, Li Xingwei, Liu Bingxian
机构信息
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
出版信息
J Org Chem. 2023 Dec 1;88(23):16330-16339. doi: 10.1021/acs.joc.3c01840. Epub 2023 Nov 15.
Bridged isoxazolidines were synthesized via Rh(III)-catalyzed C-H allylation of α-aryl nitrones with 5-methylene-1,3-dioxan-2-one. The nitrone group serves as a directing group and 1,3-dipole in the C-H activation/[3 + 2] cycloaddition cascade, exhibiting excellent chemo- and stereoselectivity along with good functional group compatibility. The resulting skeletal structure was conveniently modified to produce a range of important chemical frameworks, and the protocol was applied to biologically active molecules.
通过铑(III)催化α-芳基硝酮与5-亚甲基-1,3-二氧杂环己烷-2-酮的C-H烯丙基化反应合成了桥连异恶唑烷。硝酮基团在C-H活化/[3 + 2]环加成串联反应中作为导向基团和1,3-偶极子，表现出优异的化学和立体选择性以及良好的官能团兼容性。所得的骨架结构可方便地进行修饰以产生一系列重要的化学骨架，并且该方法已应用于生物活性分子。
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