REGIO- AND STEREODIRECTIVITY IN THE REACTIONS OF ISOQUINOLINIUM YLIDES WITH UNSATURATED NITRILES

Article abstract of DOI:10.1007/BF00958850

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-tetrahydropyrrolo<2,1-a>isoquinolines.In contrast, N-phenacylisoquinolinium ylide reacts with arylmethylenecyanothioacetamides 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.