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Updated: Sep 28, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Enantioselective Organocopper-Catalyzed Hetero Diels-Alder Reaction through in Situ Oxidation of Ethers into Enol
Ahmet Yesilcimen1, Na-Chuan Jiang1, Felix H Gottlieb1
1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
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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