Lukasevics Lukass, Cizikovs Aleksandrs, Grigorjeva Liene
Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia.
Org Lett. 2020 Apr 3;22(7):2720-2723. doi: 10.1021/acs.orglett.0c00672. Epub 2020 Mar 17.
An efficient method for the synthesis of 3-hydroxymethyl isoindolinones via cobalt-catalyzed C(sp)-H carbonylation of phenylglycinol derivatives using picolinamide as a traceless directing group is demonstrated. The reaction proceeds in the presence of a commercially available cobalt(II) tetramethylheptanedionate catalyst and employs DIAD as a "CO" surrogate. This synthetic route offers a broad substrate scope, excellent regioselectivity, and full preservation of the original stereochemistry. Besides, the developed method provides a pathway for accessing valuable enantiopure 3-substituted isoindolinone derivatives.
展示了一种通过使用吡啶甲酰胺作为无痕导向基团，钴催化苯基甘醇衍生物的C(sp)-H羰基化反应合成3-羟甲基异吲哚啉酮的有效方法。该反应在市售的四甲基庚二酸钴(II)催化剂存在下进行，并使用偶氮二甲酸二异丙酯（DIAD）作为“CO”替代物。这条合成路线具有广泛的底物范围、出色的区域选择性，并且能完全保留原始立体化学。此外，所开发的方法为获得有价值的对映体纯3-取代异吲哚啉酮衍生物提供了一条途径。
