Triethyamine‐promoted [5+3] Cycloadditions for Regio‐ and Diastereoselective Synthesis of Functionalized aza‐Bicyclo[3.3.1]alkenones
Jing Huang, Bo Jiang, Xiyuan Zhang, Yanfeng Gao, Xiufang Xu, Zhiwei Miao
Abstract
Abstract We have developed a synthetic strategy for Et 3 N‐promoted [5+3] cycloaddition reactions between acetoxypyranones and azomethine imines to access functionalized azabicyclo[3.3.1]alkenones with three tertiary stereocenters (31 examples, 36% to 87% yield, 5.5:1 to >20:1 dr). The method was scalable, and the products could be transformed to various eight‐membered‐ring bridged heterocyclic molecules. magnified image
Topics & Concepts
ChemistryStereocenterCycloadditionYield (engineering)Bicyclic moleculeRing (chemistry)StereochemistryCombinatorial chemistryOrganic chemistryEnantioselective synthesisCatalysisMaterials scienceMetallurgyOxidative Organic Chemistry ReactionsAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms