Abstract
The application of allylic sulphoxides and, particularly, the chiral amine reagent tert-butanesulphinamide has been extended to three different tandem processes. The condensation of (R)-(+)-allyl p-tolyl sulphoxide, fluorinated nitriles and alkyl propiolates led to a new family of enantiomerically pure fluorine-containing 1,4- dihydropyridines. A diastereoselective nucleophilic addition of fluorinated nucleophiles onto (R)-(tert-butanesulphinyl) imines, followed by an intramolecular aza-Michael reaction gave rise to either fluorinated isoindolines or 3-substituted indanones in a stereoselective manner.
GRAPHICAL ABSTRACT
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Acknowledgments
This work was supported by the Ministerio de Ciencia e Innovación of Spain (CTQ2010-19774) and Generalitat Valenciana (GV/PROMETEO/2010/061). P. Barrio and S. Catalán-Muñoz express their thanks for a Juan de la Cierva contract.