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

Manuel Andreini (1) , Fabien Chapellas (1) , Sonia Diab (1) , Karine Pasturaud (1) , Serge Piettre (1) , Julien Legros (1) , Isabelle Chataigner (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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.

Domains: Chemical Sciences

Manuel Andreini, Fabien Chapellas, Sonia Diab, Karine Pasturaud, Serge Piettre, et al.. Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: An unprecedented dearomatizing process. Organic & Biomolecular Chemistry, 2016, 14 (10), pp.2833-2839. ⟨10.1039/c5ob02595h⟩. ⟨hal-02046184⟩