Asymmetric Tandem Reactions: New Strategies and Applications

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

Keywords:

• Tandem reaction
• aza-Michael addition
• chiral sulphoxides
• sulphinamide
• fluorinated dihydropyridine
• fluorinated isoindoline
• indanone

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.