Enantioselective Organocopper-Catalyzed Hetero Diels–Alder Reaction through <i>in Situ</i> Oxidation of Ethers into Enol Ethers
Ahmet Yeşilçimen, Na‐Chuan Jiang, Felix H. Gottlieb, Masayuki Wasa
Abstract
We disclose a catalytic method for the enantio- and diastereoselective union of alkyl ethers and heterodienes. We demonstrate that a chiral Cu–BOX complex catalyzes the efficient oxidation of ethers into enol ethers in the presence of trityl acetate. Then, the organocopper promotes stereoselective hetero Diels–Alder reaction between the in situ generated enol ethers and β,γ-unsaturated ketoesters, allowing for rapid access to an array of dihydropyran derivatives possessing three vicinal stereogenic centers.
Topics & Concepts
ChemistryEnolStereocenterEnantioselective synthesisCatalysisDihydropyranStereoselectivityOrganic chemistryVicinalDiels–Alder reactionEnol etherAlkylCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsAxial and Atropisomeric Chirality Synthesis