Copper-Catalyzed Asymmetric Reductions of Aryl/Heteroaryl Ketones under Mild Aqueous Micellar Conditions
David M. Fialho, Elham Etemadi‐Davan, Olivia C. Langner, Balaram S. Takale, Amol V. Gadakh, Ganesh Sambasivam, Bruce H. Lipshutz
Abstract
Enantioselective syntheses of nonracemic secondary alcohols have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)2·H2O/(R)-3,4,5-MeO-MeO-BIPHEP) reduction of aryl/heteroaryl ketones. This methodology serves as a green protocol to access enantio-enriched alcohols under mild conditions (0–22 °C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alcohol products are formed in good to excellent yields with ee values greater than 90%.
Topics & Concepts
ChemistryCatalysisArylAqueous solutionCopperStoichiometryAlcoholBase (topology)HydrideEnantioselective synthesisOrganic chemistryCombinatorial chemistryAqueous mediumMetalAlkylMathematical analysisMathematicsAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisNanomaterials for catalytic reactions