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Construction of Chiral-Fused Tricyclic γ‑Lactams via a trans-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction

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posted on 12.05.2017, 15:20 by Qianjin An, Jiefeng Shen, Delong Liu, Yangang Liu, Wanbin Zhang
An asymmetric domino reaction was developed utilizing readily available cyclic α-dehydroamino ketones and aldehydes, which when subjected a 2-iodoxybenzoic acid (IBX)-mediated oxidation gives pyrrolidinone-containing tricyclic derivatives. trans-Perhydroindolic acid proved to be an efficient organocatalyst in this reaction (up to 94% yield, 99% ee, and >20:1 dr). The product could be conveniently converted to synthetically useful intermediates via simple transformations. A possible stereocontrolled process has been suggested according to X-ray crystallography studies.