Organic Letters
Organic Letters
5 years ago

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

Construction of Chiral-Fused Tricyclic γ-Lactams via a trans-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction
Yangang Liu, Qianjin An, Wanbin Zhang, Jiefeng Shen, Delong Liu
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01160

DOI: 10.1021/acs.orglett.7b01160

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