Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles
Wang Bi, Jing-Kun Gao, Shuo Sun, Zhenlu Shen, Yun‐Fang Yang, Ren‐Xiao Liang, Yi‐Xia Jia
Abstract
An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of N -( o -bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba) 2 /SPINOL-based phosphoramidite as the chiral catalyst and HCO 2 Na as the hydride source, a series of enantioenriched spiro indolines bearing vicinal stereocenters were afforded in moderate to good yields with excellent enantioselectivities. The reductive Heck reaction of formal tetrasubstituted alkene bearing β-hydrogens is therefore realized by inhibiting β-H elimination.
Topics & Concepts
ChemistryIntramolecular forceStereocenterHeck reactionEnantioselective synthesisCatalysisPhosphoramiditeAlkeneVicinalIndole testCombinatorial chemistryMedicinal chemistryOrganic chemistryPalladiumDNAOligonucleotideBiochemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions