Sc(OTf)3-Catalyzed Precise Construction of Medium-Sized [4.2.1]-Oxabridged Scaffolds
Dong-Sheng Ji1, Chenxing Zhou1, Xudong Wang1
1College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.
Abstract:
In this study, the readily available and inexpensive Sc(OTf)3 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.
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