Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles,The Journal of Organic Chemistry

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Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-12-20 , DOI: 10.1021/acs.joc.4c02363
Liang-Chen Ren, Min Wang, Xiao Zha, Yu-Rui Jian, Li-Ren Zhang, Jia-Jing Tan, Bao-Dong Cui, Yun Zhang, Xue-Qing Mou, Yong-Zheng Chen

A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO₂- and Ar₂CN-functionalized O-heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH₂- and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions. Importantly, the efficient conversion of secondary alcohol products to amines with complete inversion of configuration enhances the methodology, enabling the construction of 2-aryl-3-amino tetrahydrofuran with high and complementary diastereoselectivity.

更新日期：2024-12-20

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