Enantioselective Organocopper-Catalyzed Hetero Diels–Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers
Journal of the American Chemical Society2022Vol. 144(14), pp. 6173–6179
Citations Over TimeTop 15% of 2022 papers
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.
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