Ir-Catalyzed Asymmetric Tandem Allylation/<i>Iso</i>-Pictet–Spengler Cyclization Reaction for the Enantioselective Construction of Tetrahydro-γ-carbolines
Fan Xiao, Shiming Xu, Xiu‐Qin Dong, Chun‐Jiang Wang
Abstract
-Pictet-Spengler cyclization of arylidenaminomalonates with indolyl allylic methyl carbonates was successfully developed, which provided a direct and practical approach to access synthetically useful and biologically active tetrahydro-γ-carboline derivatives bearing multiple functional groups and stereogenic centers in good to high yields and excellent stereoselective control (44%-96% yields, >20:1 dr, 94% → 99% ee). A wide range of substrate generality, easily available substrates, and simple chiral catalytic system displayed great potential practicality of this efficient protocol.
Topics & Concepts
ChemistryEnantioselective synthesisPictet–Spengler reactionTandemCatalysisCascade reactionCombinatorial chemistryStereochemistryOrganic chemistryComposite materialMaterials scienceSynthesis and bioactivity of alkaloidsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis