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

2024/12/19 by Dongsheng Ji, Dong-Sheng Ji, Chenxing Zhou +4 · 6 citations
Chemistry · #Catalysis #Catalytic Cross-Coupling Reactions #Chemistry #Combinatorial chemistry #Computer science #Cyclopropane Reaction Mechanisms #Organic chemistry #Synthetic Organic Chemistry Methods

paper · doi:10.1021/acs.joc.4c02657

published in The Journal of Organic Chemistry 90(1), 716-721 (American Chemical Society)

openalex publication_date 2024/12/19 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

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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