Tetrahedron

The fluoride ion-induced intramolecular conjugate addition of propargylsilanes to dihydropyridones. A novel method for the stereoselective construction of azabicyclic …

M Dziedzic, G Lipner, JM Illangua, B Furman

Index: Dziedzic, Magdalena; Lipner, Grzegorz; Illangua, Jose M.; Furman, Bartlomiej Tetrahedron, 2005 , vol. 61, # 36 p. 8641 - 8647

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Citation Number: 9

Abstract

The fluoride ion-induced intramolecular conjugate addition of propargylsilanes to dihydropyridones is reported. Our results revealed that tetrabutylammonium triphenyldifluorosilicate (TBAT), an air-stable, non-hygroscopic fluoride ion source, catalyzes cyclocondensation to provide the corresponding 1-vinylidene indolizidines in a high yield as single isomers, while Lewis acid catalysts were ineffective. The scope of this method was ...