Yu Jing-Liang, Zhang Qian-Mao, Cheng Guo, Tang Chun-Chun, Yang Zhen-Yu, Li Wen-Sheng, Wang Li-Xin
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
Org Biomol Chem. 2024 Sep 25;22(37):7612-7617. doi: 10.1039/d4ob01175a.
A highly effective and enantioselective vinylogous Mannich reaction between benzothiazolimines and γ-butenolides catalyzed by a quinine based squaramide has been disclosed. A series of chiral benzothiazole amines containing a γ,γ-disubstituted butanolide scaffold bearing an adjacent chiral stereocenter have been successfully obtained in good to excellent yields (up to 91%) with excellent enantioselectivities (up to >99% ee) and diastereoselectivities (>20 : 1 dr) with broad substrate generality under mild conditions. The new scaffold integrated with both chiral benzothiazolimine and γ-butenolide moieties may provide a possibility for the development of new pharmaceutical entities.
已披露一种由基于奎宁的方酰胺催化的苯并噻唑亚胺与γ-丁内酯之间高效且对映选择性的乙烯基曼尼希反应。在温和条件下，一系列含有带有相邻手性立体中心的γ,γ-二取代丁内酯骨架的手性苯并噻唑胺已成功以良好至优异的产率（高达91%）、优异的对映选择性（高达>99% ee）和非对映选择性（>20:1 dr）以及广泛的底物通用性获得。与手性苯并噻唑亚胺和γ-丁内酯部分整合的新骨架可能为开发新的药物实体提供可能性。
