ChemInform Abstract: Synthesis and Dienophilic Behavior of Enantiomerically Pure (Z)‐3‐p‐Tolylsulfinylacrylonitriles.

Abstract

Synthesis and Dienophilic Behavior of Enantiomerically Pure (Z)-3-p-Tolylsulfinylacrylonitriles.-Under thermal as well as catalytic ZnBr 2 conditions the title nitriles (IIIa)-(IIIc) react with the diene (IV) to afford the adducts (V) and (VI) with complete π-facial diastereoselectivity.In the presence of BF 3 ·OEt 2 the π-facial diastereoselectivity can be totally reversed. Interestingly, in the latter case exclusive formation of the endo-adducts (VII) takes place with concomitant inversion of the sulfur configuration. -(GARCIA RUANO, J. L.; ESTEBAN GAMBOA, A.; MARTIN CASTRO, A. M.; RODRIGUEZ, J. H.; LOPEZ-SOLERA, M. I.; J.