ol7b01160_si_005.cif (378.21 kB)
Construction of Chiral-Fused Tricyclic γ‑Lactams via a trans-Perhydroindolic Acid-Catalyzed Asymmetric Domino Reaction
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posted on 2017-05-12, 15:20 authored by Qianjin An, Jiefeng Shen, Delong Liu, Yangang Liu, Wanbin ZhangAn 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.
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ee2- iodoxybenzoic acidIBXX-ray crystallography studiesPerhydroindolic aciddomino reactionsyntheticallyConstructionpyrrolidinone-containing tricyclic derivativesaldehydeLactamtransformationoxidationChiral-Fusedintermediatestereocontrolled processTricyclictranPerhydroindolic Acid-Catalyzed Asymmetric Domino Reactionorganocatalystcyclic α- dehydroamino ketones