Gold/Chiral Amine Relay Catalysis Enables Asymmetric Synthesis of C2-Quaternary Indolin-3-ones
Wenbin Wang, Ji-Chao Lu, Hao Bai, Yanming Fu, Lanjun Cheng, Chengfeng Zhu, Yougui Li, Xiang Wu
Abstract
A mild and effective strategy for the asymmetric synthesis of C2-quaternary indolin-3-ones from 2-alkynyl arylazides and ketones by gold/chiral amine relay catalysis is described. In this reaction, 2-alkynyl arylazides undergo gold-catalyzed cyclization, nucleophilic attack, and oxidation to form intermediate 2-phenyl-3 H -indol-3-ones, followed by an l -proline-catalyzed asymmetric Mannich reaction with ketones, to afford corresponding products in satisfactory yields with excellent enantio- and diastereoselectivities.
Topics & Concepts
ChemistryCatalysisNucleophileAmine gas treatingMannich reactionCombinatorial chemistryEnantioselective synthesisReaction conditionsOrganic chemistryCatalytic Alkyne ReactionsChemical synthesis and alkaloidsOxidative Organic Chemistry Reactions