title: Stereoselective C9 arylation and vinylation of Cinchona alkaloids.
abstract: A simple and efficient method for the highly stereoselective C-9 arylation and vinylation of Cinchona alkaloids was developed. Both 9S- and 9R-chloroquinine with PhMgBr yielded 9S-phenylquinine (X-ray structure). The reactions with various aryl and vinyl Grignard reagents resulted in the series of 9S-aryl and vinyl alkaloid derivatives. The stereochemical outcome was rationalized by coordination of the magnesium atom to the quinuclidine nitrogen, thus directing the nucleophilic attack at the C-9 stereogenic center.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, 50-370 Wrocław, Poland.
authors.forename: Przemysław J
authors.initials: PJ
authors.lastname: Boratyński
authors.forename: Ilona
authors.initials: I
authors.lastname: Turowska-Tyrk
authors.forename: Jacek
authors.initials: J
authors.lastname: Skarzewski
mesh_terms: D002930:Cinchona Alkaloids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D002930:Cinchona Alkaloids; D006843:Hydrocarbons, Chlorinated; D014753:Vinyl Compounds