Diastereoselective Synthesis of Pyrroloquinolines via N–H Functionalization of Indoles with Vinyl Sulfonium Salts
Ruiying Ma, Zijie Zhou, Peng Yang, Ling Ye, Zhichuan Shi, Zhigang Zhao, Xuefeng Li
Abstract
A [2 + 4]/[1 + 2] annulation approach was successfully established to construct pyrroloquinoline-fused cyclopropane in a highly diastereoselective fashion (>20:1 dr). The tetracyclic 1,7-fused indoles were efficiently obtained from readily available starting materials under mild conditions. This methodology displays impressive substrate generality with two reaction components. The products resulting from this doubly annulative strategy are useful synthetic intermediates.
Topics & Concepts
SulfoniumAnnulationChemistryCyclopropaneSurface modificationSubstrate (aquarium)Combinatorial chemistryOrganic chemistryStereochemistryCatalysisRing (chemistry)OceanographySalt (chemistry)Physical chemistryGeologyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions