A Bispidine-Based Chiral Amine Catalyst for Asymmetric Mannich Reaction of Ketones with Isatin Ketimines
A Bispidine-Based Chiral Amine Catalyst for Asymmetric Mannich Reaction of Ketones with Isatin Ketimines
复制标题
基于双吡啶的手性胺催化剂用于酮与靛红酮亚胺的不对称曼尼希反应
DOI：
10.1021/acs.orglett.0c03305
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发表时间：
2020-11-06
期刊：
影响因子：
5.2
通讯作者：
Lin, Lili
中科院分区：
文献类型：
--
作者：
Li, Gonglin;Liu, Mohuizi;Lin, Lili
一种独特的具有双吡啶结构的手性有机胺催化剂被发现是有效的非对映和对映选择性的靛红酮亚胺与酮的Mannich反应。合成了一系列3-取代的3-氨基-2-羟吲哚类化合物，它们具有邻位叔、季手性中心，产率高，dr和ee值高。克级合成及产物的转化证明了该方法的实用性。此外，提出了一个可能的过渡态模型来解释立体选择性的起源。
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.