Steric, Electronic and Conformational Synergistic Effects in the Gold(I)‐catalyzed α <i>‐</i> C−H Bond Functionalization of Tertiary Amines**
David Fabian León Rayo, Ali Mansour, Wenbin Wu, Benjamin N. Bhawal, Fabien Gagosz
Abstract
Direct C-H bond functionalization is a useful strategy for the straightforward formation of C-C and C-Heteroatom bonds. In the present work, a unique approach for the challenging electrophilic Au-catalyzed α-C-H bond functionalization of tertiary amines is presented. Electronic, steric and conformational synergistic effects exerted by the use of a malonate unit in the substrate were key to the success of this transformation. This new reactivity was applied to the synthesis of tetrahydro-γ-carboline products which, under oxidative conditions, could be converted into valuable structural motifs found in bioactive alkaloid natural products.
Topics & Concepts
Steric effectsChemistrySurface modificationElectrophileHeteroatomReactivity (psychology)Combinatorial chemistrySubstrate (aquarium)StereochemistryCatalysisOrganic chemistryRing (chemistry)Alternative medicinePathologyMedicineOceanographyGeologyPhysical chemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsAsymmetric Hydrogenation and Catalysis