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

作者：An, Qianjin; Shen, Jiefeng; Butt, Nicholas; Liu, Delong^*; Liu, Yangang; Zhang, Wanbin

来源：Organic Letters, 2014, 16(17): 4496-4499.

DOI：10.1021/ol502033v

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 add 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.

• 出版日期2014-9-5
• 单位上海交通大学