Diels-Alder cycloadditions using nucleophilic 2-pyridones. Regiocontrolled and stereocontrolled synthesis of unsaturated, bridged, bicyclic lactams

GH Posner, V Vinader, K Afarinkia

Index: Posner, Gary H.; Vinader, Victoria; Afarinkia, Kamyar Journal of Organic Chemistry, 1992 , vol. 57, # 15 p. 4088 - 4097

Full Text: HTML

Citation Number: 44

Abstract

Captodative% oxy-and 3-(tolylthio)-l-tusyl-2-pyridones la-ld are shown to be reactive as nucleophilic dienes undergoing 2+ 4-cycloadditions with various electrophilic alkenes under sufficiently mild thermal conditions (W100" C) that the initial bicylic lactam adducts can be isolated on gram de in fair to very good yields (23-83%) without loss of an isocyanate from the heteroatom bridge. These bicyclic adducts are formed with complete regiocontrol and ...