Regio- and stereodirectivity in the reactions of isoquinolinium ylides with unsaturated nitriles

Reactions of isoquinolinium ylides with arylmethylenemalonitriles involve 1,3-dipolar cycloaddition, with the highly regio- and stereoselective formation of 2-aryl-3-benzoyl(or carbamoyl)1,1-dicyano-2,3-trans-1,2,3,10b-tetrahydropyrrolo2, 1-a]isoquinolines. In contrast, N-phenacylisoquinolinium ylide reacts with aryl-methylenecyanothioacetamides differently, proceeding regio- and stereoselectively to give 4-aryl-2-hydroxy-3-(1-isoquinolinio)-2-phenyl-3-cyano-3,4-trans-1,2,3,4-tetrahydropyridine-6-thiolates.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2593–2599, November, 1990.