title: One-pot synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a Et3N-promoted pseudo five-component reaction.
abstract: An effective and practical method has been developed for the diversity-oriented synthesis of fully substituted cyclohexene β-aminoester via a pseudo five-component reaction between nitromethane, aromatic aldehydes, and substituted cyanoacetate for the generation of a wide range of structurally relevant and highly functionalized compounds. The attractive range and features of the method, which enables the facile preparation of highly substituted cyclohexenes, are its simple and straightforward procedure, mild reaction conditions, and ideal yields. The mechanism involves a double Michael addition reaction followed by intramolecular ring closure. The fully substituted cyclohexene β-aminoesters with potential bioactivities could be of impact in medical chemistry.
authors.affiliation: School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou, 225002, Jiangsu, People's Republic of China.
authors.forename: Juan
authors.initials: J
authors.lastname: Yao
authors.forename: Lanxiang
authors.initials: L
authors.lastname: Zhou
authors.forename: Chen
authors.initials: C
authors.lastname: Tan
authors.forename: Cunde
authors.initials: C
authors.lastname: Wang
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D053138:Cyclohexenes / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D009595:Nitroparaffins / Q000737:chemistry*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D053138:Cyclohexenes; D004952:Esters; D009595:Nitroparaffins; D008697:Methane; C008640:nitromethane