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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