Copper‐Catalyzed Asymmetric 1,6‐Addition of Borylalkene‐Derived Nucleophiles to <i>para</i>‐Quinone Methides
Deyuan Meng, Jing He, Woojin Yoon, Hoseop Yun, Jung Tae Han, Jaesook Yun
Abstract
Abstract Herein, we report the catalytic 1,6‐addition of chiral alkyl copper nucleophiles, in‐situ generated from borylalkenes and a copper‐hydride catalyst under mild conditions. Chemo‐ and stereoselective control was crucial in this reductive coupling process of borylalkenes and para ‐quinone methides, sequentially forming adjacent stereogenic centers with good diastereo‐ and enantioselectivity. Through the multicomponent and catalytic tandem reactions, asymmetric 1,6‐adducts of p ‐quinone methides were efficiently synthesized. magnified image
Topics & Concepts
ChemistryStereocenterNucleophileQuinoneCatalysisQuinone methideCopperAdductEnantioselective synthesisStereoselectivityAlkylCombinatorial chemistryTandemHydrideMedicinal chemistryOrganic chemistryComposite materialMaterials scienceHydrogenSynthesis of Indole DerivativesSulfur-Based Synthesis Techniques