Chiral Brønsted Acid-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Indoles with Primary Alcohols
Lei-Ming Zou, Xian-Yun Huang, Chao Zheng, Yuan‐Zheng Cheng, Shu‐Li You
Abstract
Herein, chiral Brønsted acid-catalyzed intramolecular asymmetric allylic alkylation of indoles with allylic primary alcohols is described. The allyl alcohols were directly employed as the allylic precursors in this metal-free protocol, without preactivation or any additional activating reagents. This method provides the convenient synthesis of a broad range of functionalized tetrahydrocarbazoles in excellent yields (≤97%) with good enantioselectivity (≤93% ee). The optimal conditions are compatible for gram-scale reaction.
Topics & Concepts
ChemistryIntramolecular forceAllylic rearrangementTsuji–Trost reactionBrønsted–Lowry acid–base theoryCatalysisReagentAlkylationCombinatorial chemistryOrganic chemistryPrimary (astronomy)AstronomyPhysicsAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisAlkaloids: synthesis and pharmacology