Synthesis of Oxo-Bridged Dibenzoazocines through Ruthenium-Catalyzed [4 + 3]-Cycloannulation of Aza-<i>ortho</i>-quinone Methides with Carbonyl Ylides
Pengfei Jia, Zhiqian Lin, Shenmeng Yan, Jiao Liang, Cankun Luo, Ruizhi Lai, Li Hai, Zhongzhen Yang, Yong Wu
Abstract
Oxo-bridged dibenzoazocines are furnished within a single synthetic step at room temperature via ruthenium-catalyzed [4 + 3]-cycloannulation of aza- ortho -quinone methides with carbonyl ylides. Exclusive diastereoselectivity, excellent yield, mild reaction conditions, and broad substrate scope are distinguishing features of this protocol. The product could be prepared on a gram scale and could be further functionalized into diverse substituted dihydroisobenzofuran derivatives and a dibenzoazocine scaffold.
Topics & Concepts
ChemistryRutheniumYield (engineering)CatalysisSubstrate (aquarium)QuinoneCombinatorial chemistryAnnulationStereochemistryOrganic chemistryGeologyOceanographyMetallurgyMaterials scienceSynthesis of Indole DerivativesCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques