Asymmetric Synthesis of Hydroindoles via Desymmetrizing [3+2] Annulation of <i>p</i>-Quinamines and Arylalkylketenes
Qianping Chen, Yan Zhang, Yanji Song, Yang Zhang, Zhishan Su, Xiaoming Feng, Xiaohua Liu
Abstract
-quinamines and arylalkylketenes to synthesize hydroindoles was realized. Catalyzed by chiral bisguanidinium hemisalt via multiple hydrogen bond interactions, enantiomerically enriched products with reversal of diastereoselectivity in comparison with the racemic version were afforded in good yields under mild reaction conditions. Diaryl-substituted hydroindoles could also perform the Friedel-Crafts type of addition to give more complicated multicycles. Density functional theory calculations revealed that the enantio- and diastereoselectivity stem from varied hydrogen-bonding manners.
Topics & Concepts
ChemistryAnnulationEnantioselective synthesisHydrogen bondDensity functional theoryCatalysisCombinatorial chemistryStereochemistryOrganic chemistryMedicinal chemistryComputational chemistryMoleculeAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsSynthesis and Catalytic Reactions