期刊
ORGANIC LETTERS
卷 16, 期 17, 页码 4496-4499出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol502033v
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资金
- National Natural Science Foundation of China [21172143, 21172145, 21372152, 21232004]
- Nippon Chemical Industrial Co., Ltd.
- Shanghai Jiao Tong University (SJTU)
- Instrumental Analysis Center of SJTU
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.
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