Eidgenössische Technische Hochschule (ETH) Zürich, Building HCI, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.
Org Lett. 2021 Apr 2;23(7):2643-2647. doi: 10.1021/acs.orglett.1c00559. Epub 2021 Mar 22.
A method for the enantio- and chemoselective iridium-catalyzed -allylation of oximes is described. Kinetic resolution in an intramolecular setting provides enantioenriched oxime ethers and aliphatic allylic alcohols. The synthetic potential of the products generated with this method is showcased by their elaboration into a series of heterocyclic compounds and the formal synthesis of glycoprotein GP IIb-IIIa receptor antagonist (-)-roxifiban. Preliminary mechanistic experiments and computational data shed light on the remarkable chemoselectivity of the reaction.
描述了一种对映选择性和化学选择性的铱催化肟的 -烯丙基化方法。动力学拆分在分子内环境中提供了对映体富集的肟醚和脂肪族烯丙醇。通过该方法生成的产物的合成潜力通过将其精心制备成一系列杂环化合物和糖蛋白 GP IIb-IIIa 受体拮抗剂 (-)-roxifiban 的形式合成来展示。初步的机理实验和计算数据阐明了反应的显著化学选择性。
