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Asymmetric Domino Reaction of Cyclic N‑Sulfonylimines and Simple Aldehydes with trans-Perhydroindolic Acid as an Organocatalyst

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journal contribution
posted on 05.09.2014, 00:00 by Qianjin An, Jiefeng Shen, Nicholas Butt, Delong Liu, Yangang Liu, Wanbin Zhang
An asymmetric domino reaction was developed utilizing readily available cyclic N-sulfonylimines and simple aldehydes to construct biologically important and synthetically challenging piperidine derivatives consisting of three contiguous stereocenters. trans-Perhydroindolic acid proved to be an efficient organocatalyst in this reaction (up to 89% yield, 80:20 dr, and 99% ee). The absolute configuration of the catalytic product was determined by X-ray crystallography studies. The product could be conveniently converted to synthetically useful intermediates, such as (3R,4S)-4-ethyl-3-methyl-6-phenylpiperidinyridin-2-one (8), via a simple transformation.