College of Chemistry and Chemical Engineering, Central South University , Changsha 410083, P. R. China.
J Org Chem. 2016 Sep 2;81(17):8001-8. doi: 10.1021/acs.joc.6b01356. Epub 2016 Aug 10.
Highly diastereo- and enantioselective conjugate additions of azlactones to enolizable cyclic and linear enones were conducted by employing proline aryl sulfonamide as the organocatalyst in trifluorotoluene. The conjugate adducts bearing contiguous quaternary and tertiary stereocenters were obtained in moderate to good yields with excellent diastereoselectivities and moderate to good enantioselectivities. This developed protocol filled in the substrate gap for the organocatalytic conjugate addition of azlactone to enones.
采用脯氨酸芳基磺酰胺作为有机催化剂,在三氟甲苯中进行了高非对映选择性和对映选择性的氮杂环丁酮与烯醇化的环状和线性烯酮的共轭加成反应。在中等至良好的产率下,得到了带有连续的季碳和叔碳立体中心的共轭加成产物,具有优异的非对映选择性和中等至良好的对映选择性。该方法填补了氮杂环丁酮与烯酮的有机催化共轭加成反应中底物空缺。