Stereoselective C9 arylation and vinylation of Cinchona alkaloids.
作者： Przemysław J. Boratyński , Ilona Turowska-Tyrk , Jacek Skarżewski
DOI: 10.1021/OL7026625
关键词: Nucleophile 、 Stereocenter 、 Magnesium 、 Stereoselectivity 、 Chemistry 、 Alkaloid 、 Aryl 、 Reagent 、 Organic chemistry 、 Cinchona Alkaloids
摘要: A simple and efficient method for the highly stereoselective C-9 arylation vinylation of Cinchona alkaloids was developed. Both 9S- 9R-chloroquinine with PhMgBr yielded 9S-phenylquinine (X-ray structure). The reactions various aryl vinyl Grignard reagents resulted in series 9S-aryl alkaloid derivatives. stereochemical outcome rationalized by coordination magnesium atom to quinuclidine nitrogen, thus directing nucleophilic attack at stereogenic center.
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