The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, 1200 Cailun Road, Shanghai 201203, China.
Chem Commun (Camb). 2020 Sep 15;56(73):10718-10721. doi: 10.1039/d0cc04462h.
A highly enantioselective [3+2] annulation of isatin-derived Morita-Baylis-Hillman (MBH) carbonates and 3-nitroindoles was enabled by a chiral DMAP-thiourea bifunctional catalyst, affording the corresponding polycyclic spirooxindoles bearing three consecutive stereocenters with good to excellent yields and enantioselectivities. Transformations of the annulation product were subsequently elaborated and the preliminary biological assays demonstrated that these artificial spirooxindoles potentially inhibited pancreatic lipase in a dose-dependent manner.
手性 DMAP-硫脲双功能催化剂能够实现高对映选择性的色胺衍生的 Morita-Baylis-Hillman（MBH）碳酸酯和 3-硝基吲哚的[3+2]环加成反应，得到相应的多环螺[吲哚啉-2,3'-氧吲哚]，具有良好到优秀的收率和对映选择性。随后对环加成产物进行了转化，并进行了初步的生物活性测试，结果表明这些人工螺[吲哚啉-2,3'-氧吲哚]能够以剂量依赖的方式潜在抑制胰脂肪酶。
