Enantioselective Palladium(II)‐Catalyzed Desymmetrizative Coupling of 7‐Azabenzonorbornadienes with Alkynylanilines
Junjie Meng, Hui He, Qianru Liu, Hanhong Xu, Huicai Huang, Shao‐Fei Ni, Zhaodong Li
Abstract
-catalyzed, domino enantioselective desymmetrizative coupling of 7-azabenzonorbornadienes with alkynylanilines is disclosed herein. This operationally simple transformation generates three covalent bonds and two contiguous stereocenters with excellent enantio- and diastereo-selectivity. The resulting functionalized indole-dihydronaphthalene-amine conjugates served as an appealing platform to streamline the diversity-oriented synthesis (DOS) of other valuable enantioenriched compounds. DFT calculations revealed that the two stabilizing non-covalent interactions contributed to the observed enantioselectivity.
Topics & Concepts
Enantioselective synthesisStereocenterPalladiumDominoCombinatorial chemistryCatalysisCovalent bondChemistryAmine gas treatingConjugateTransformation (genetics)Organic chemistryMathematicsMathematical analysisGeneBiochemistryCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and Catalysis