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

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• 作者：Qianjin An ; Jiefeng Shen ; Nicholas Butt ; Delong Liu ; Yangang Liu ; Wanbin Zhang
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：September 5, 2014
• 年：2014
• 卷：16
• 期：17
• 页码：4496-4499
• 全文大小：375K
• ISSN：1523-7052

文摘

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.