Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy
Yu‐Han Nie, Masaaki Komatsuda, Ping Yang, Chao Zheng, Junichiro Yamaguchi, Shu‐Li You
Abstract
Pd-catalyzed asymmetric dearomative arylation of C3-substituted indoles is realized via a desymmetrization strategy. A BINOL-derived chiral phosphoramidite ligand is found to be highly efficient for the stereoselective control in this reaction. This method provides a convenient synthesis of spiroindolenines bearing two stereogenic centers in good yields (up to 98%) with excellent diastereo- and enantioselectivities (up to >20:1 dr and 97% ee), which could also be applied in asymmetric dearomative arylation of the simple C3-tethered indoles.
Topics & Concepts
DesymmetrizationStereocenterChemistryPhosphoramiditeCatalysisCombinatorial chemistryLigand (biochemistry)StereoselectivityEnantioselective synthesisStereochemistryOrganic chemistryReceptorOligonucleotideBiochemistryDNAAlkaloids: synthesis and pharmacologyCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis