Shi Siyu, Gu Mengyun, Chen Danna, Li Ruya, Shen Zhiqiang, Huang Jinqi, Yan Wenjin
The Institute of Pharmacology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, China.
Department of Hematology, Guangzhou First People's Hospital, Institute of Blood Transfusion and Hematology, Guangzhou Medical University, Guangzhou, Guangdong, China.
Chem Commun (Camb). 2024 Oct 1;60(79):11116-11119. doi: 10.1039/d4cc03297g.
Herein, we report an example of a stereoselective γ-addition reaction of trifluoromethyl ketimines to 1-alkynyl ketones mediated by an isothiourea, BTM, under mild conditions, which afforded tetrasubstituted allenes with central chiralities in high yields (up to 94% yield), good enantioselectivities (up to 91% ee), and excellent diastereoselectivities (all >20 : 1 dr). In addition, the BTM-catalyzed γ-addition reaction was successfully applied to the gram-scale reaction, and an unexpected benzopyrrolothiazine derivative was successfully converted, albeit racemic.
在此，我们报道了一例在温和条件下，由异硫脲BTM介导的三氟甲基酮亚胺与1-炔基酮的立体选择性γ-加成反应，该反应以高产率（高达94%）、良好的对映选择性（高达91% ee）和优异的非对映选择性（均>20:1 dr）得到了具有中心手性的四取代丙二烯。此外，BTM催化的γ-加成反应成功应用于克级反应，并且意外地将一种苯并吡咯并噻嗪衍生物成功转化，尽管是外消旋体。
