Sc(OTf) 3 -Catalyzed Precise Construction of Medium-Sized [4.2.1]-Oxabridged Scaffolds

In this study, the readily available and inexpensive Sc(OTf) was utilized to activate ortho-benzoyl diazo compounds to in situ generate highly reactive cyclic 1,3-dipoles, which underwent a regioselective [4 + 3] cycloaddition with dioxopyrrolidines, yielding the [4.2.1]-oxabridged scaffolds bearing...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-12
Main Authors: Ji, Dong-Sheng, Zhou, Chenxing, Wang, Xudong, Bao, Xiazhen, Yuan, Yong, Huo, Congde
Format: Article
Language:English
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Summary:In this study, the readily available and inexpensive Sc(OTf) was utilized to activate ortho-benzoyl diazo compounds to in situ generate highly reactive cyclic 1,3-dipoles, which underwent a regioselective [4 + 3] cycloaddition with dioxopyrrolidines, yielding the [4.2.1]-oxabridged scaffolds bearing multiple contiguous quaternary carbon centers with high diastereoselectivities. The method not only exhibited significant economic and operational advantages but also demonstrated practical value through gram-scale synthesis and derivatization experiments.
ISSN:1520-6904