Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5 + 2] Annulation of o-Arylanilines with Dienes

• DOI: 10.1021/acs.orglett.7b00503
• Publication Date: 2017-03-15T14:56:30Z
• Authors: Lu Bai; Yan Wang; Yicong Ge; Jingjing Liu; Xinjun Luan
• Keywords: Stereocenter; Annulation; Diene

An efficient method for the construction of dibenzo[b,d]azepines containing two distinct stereogenic elements in a highly diastereoselective fashion is described. The key [5 + 2] reaction to form π-allylpalladium species through sequential C-H activation and regiospecific migratory insertion diene. This observation contrasts with behavior 1,2-alkenes that generally underwent direct alkenylation via β-hydride elimination.