Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: an unprecedented dearomatizing process

Nucleophilic enamines add spontaneously on heteroarenes 3-nitroindole and benzofuran to form a new C-C bond. With nitroindole 1 and enamine 2a , an unprecedented dearomatizing formal ene reaction occurs in a totally regio- and diastereo-selective manner. With 3-nitrobenzofuran 10 and enamine 2d , the reaction course is different and leads to the generation of a dienylphenol. Nucleophilic enamine 2a add spontaneously on nitroindole 1 to form a dearomatized formal ene adduct 3a .