Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
J Am Chem Soc. 2022 Apr 13;144(14):6173-6179. doi: 10.1021/jacs.2c01656. Epub 2022 Apr 5.
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 generated enol ethers and β,γ-unsaturated ketoesters, allowing for rapid access to an array of dihydropyran derivatives possessing three vicinal stereogenic centers.
我们公开了一种手性铜-BOX 配合物催化的烷基醚和杂二烯的对映选择性和非对映选择性的联合方法。我们证明,在三苯乙酰氧基乙酸酯存在的情况下,手性 Cu-BOX 配合物可以有效地将醚氧化为烯醇醚。然后,有机铜促进生成的烯醇醚与β,γ-不饱和酮酯之间的立体选择性杂 Diels-Alder 反应,从而快速获得一系列具有三个相邻立体中心的二氢吡喃衍生物。