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Stereoselective C9 Arylation and Vinylation of Cinchona Alkaloids

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journal contribution
posted on 07.02.2008, 00:00 by Przemysław J. Boratyński, Ilona Turowska-Tyrk, Jacek Skarżewski
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.