Li Gonglin, Liu Mohuizi, Zou Sijia, Feng Xiaoming, Lin Lili
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Org Lett. 2020 Nov 6;22(21):8708-8713. doi: 10.1021/acs.orglett.0c03305. Epub 2020 Oct 19.
A unique chiral amine organocatalyst with a bispidine structure was found to be efficient for the diastereo- and enantioselective Mannich reaction of isatin ketimines with ketones. A series of 3-substituted 3-amino-2-oxindoles bearing vicinal tertiary and quaternary chiral stereogenic centers were obtained in excellent yields with excellent dr and ee values. The gram-scale synthesis and transformation of the product showed the practicability of this methodology. In addition, a possible transition state model was proposed to explain the origin of the stereoselectivity.
一种具有联吡啶结构的独特手性胺有机催化剂被发现对异吲哚酮亚胺与酮的非对映和对映选择性曼尼希反应有效。一系列带有相邻叔碳和季碳手性立体中心的3-取代-3-氨基-2-氧化吲哚以优异的产率、非对映选择性和对映体过量值得到。产物的克级合成及转化表明了该方法的实用性。此外，还提出了一个可能的过渡态模型来解释立体选择性的起源。
