Construction of Chiral-Fused Tricyclic γ‑Lactams via a trans-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction
datasetposted on 12.05.2017, 15:20 authored 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.
Read the peer-reviewed publication
ee2- iodoxybenzoic acidIBXX-ray crystallography studiesPerhydroindolic aciddomino reactionsyntheticallyConstructionpyrrolidinone-containing tricyclic derivativesaldehydeLactamtransformationoxidationChiral-Fusedintermediatestereocontrolled processTricyclictranPerhydroindolic Acid-Catalyzed Asymmetric Domino Reactionorganocatalystcyclic α- dehydroamino ketones