Catalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition of 1-thioaurones and 1-azaaurones
Shu‐Pei Yuan, Pei‐Hao Dou, Yun‐Qing Jia, Jian‐Qiang Zhao, Yong You, Zhen‐Hua Wang, Ming‐Qiang Zhou, Wei‐Cheng Yuan
Abstract
Using 1-thioaurones and 1-azaaurones as electron-deficient oxa-dienes, an organocatalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition with γ-deconjugated butenolides and azlactones was developed. A wide range of optically active benzothiophene-fused δ-lactones and indole-fused δ-lactones were obtained with desirable outcomes (up to 94% yield, >99 : 1 dr and 99% ee).
Topics & Concepts
CycloadditionChemistryEnantioselective synthesisYield (engineering)InverseBenzothiopheneCatalysisIndole testStereochemistryOrganic chemistryMathematicsMaterials scienceThiopheneMetallurgyGeometryOrganic Chemistry Cycloaddition ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods