title: Asymmetric domino reaction of cyclic N-sulfonylimines and simple aldehydes with trans-perhydroindolic acid as an organocatalyst.
abstract: 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.
authors.affiliation: School of Pharmacy, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, P. R. China.
authors.forename: Qianjin
authors.initials: Q
authors.lastname: An
authors.forename: Jiefeng
authors.initials: J
authors.lastname: Shen
authors.forename: Nicholas
authors.initials: N
authors.lastname: Butt
authors.forename: Delong
authors.initials: D
authors.lastname: Liu
authors.forename: Yangang
authors.initials: Y
authors.lastname: Liu
authors.forename: Wanbin
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007097:Imines; C482356:N-sulfonylimine; D013450:Sulfones