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

Abstract : 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.