Stereoselective C9 arylation and vinylation of Cinchona alkaloids |
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Authors: | Boratyński Przemysław J Turowska-Tyrk Ilona Skarzewski Jacek |
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Institution: | Department of Organic Chemistry, Faculty of Chemistry, Wroc?aw University of Technology, 50-370 Wroc?aw, Poland. |
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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. |
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