Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine
Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine
复制标题
有机阳离子催化双茚吲哚的不对称均/杂二烷基化：邻位全碳季立体中心的构建和(-)-Chimonanthidine的全合成
DOI：
10.1021/jacs.8b05386
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发表时间：
2018-08-15
影响因子：
15
通讯作者：
Tian, Jin-Miao
中科院分区：
文献类型：
--
作者：
Chen, Si-Kai;Ma, Wen-Qiang;Tian, Jin-Miao
已经设计和证明了一种新型的手性螺旋环酰胺（SPA）衍生的三唑有机催化剂，以实现各种双氧冬烷的非对称同性和异地性二重甲基化，从而实现了囊泡全碳候选体的对映选择性结构。这些反应具有出色的对映体和非对映选择性（高达99％的EE和> 20：1 DR）以及高收益率（在两个步骤上最高89％）。作为这种方法的应用，已经实现了（ - ） - 嵌合胺的第一个不对称总合成。
A novel chiral spirocyclic amide (SPA)-derived triazolium organocatalyst has been designed and demonstrated to effect asymmetric homo- and heterodialkylations of various bisoxindoles, enabling enantioselective construction of vicinal all-carbon quaternary stereocenters. These reactions feature excellent enantioand diastereoselectivities (up to 99% ee and >20:1 dr) as well as good to high yields (up to 89% over two steps). As an application of this methodology, the first asymmetric total synthesis of (-)-chimonanthidine has been achieved.