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Precise Synthesis of Diastereomers of Spiro-oxindole Derivatives through Dynamic Covalent Transformation
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2024-04-17 , DOI: 10.1021/acs.joc.3c02966
Xiao-Qian Liu 1 , Jian-Dong Zhang 1 , Shun-Jun Ji 1, 2 , Xiao-Ping Xu 1, 3
Affiliation  

In this study, [1+2+2] cyclization of tryptamine-derived isocyanides with 3-ylideneoxindoles was systematically investigated. A series of structurally complex spiro-oxindole derivatives were obtained. Characteristic dynamic covalent chemistry was observed and confirmed by experiments and density functional theory calculation. Through the regulation of the solvent, temperature, and time, the precise and stereodivergent synthesis of spiro-oxindoles was achieved.

中文翻译:

通过动态共价转化精确合成螺吲哚衍生物非对映异构体

在这项研究中,系统地研究了色胺衍生的异氰化物与3-亚基氧吲哚的[1+2+2]环化反应。获得了一系列结构复杂的螺吲哚衍生物。通过实验和密度泛函理论计算观察并证实了特征动态共价化学。通过对溶剂、温度和时间的调控,实现了螺羟吲哚的精确立体合成。
更新日期:2024-04-17
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