Gold-Catalyzed [4+3] Cycloaddition/C-H Functionalization Cascade: Regio- and Diastereoselective Route to Cyclohepta[b]indoles
Gold-Catalyzed [4+3] Cycloaddition/C-H Functionalization Cascade: Regio- and Diastereoselective Route to Cyclohepta[b]indoles
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DOI：
10.1002/ejoc.201701441
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发表时间：
2017-12-08
影响因子：
2.8
通讯作者：
Zhang, Junliang
中科院分区：
文献类型：
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作者：
Li, Yangyan;Zhu, Chao-Ze;Zhang, Junliang
首次开发了金催化的[4+3]环加成/C-H官能化级联。该反应以优异的产率有效地获得密集官能化的环庚[b]吲哚，其中第二种炔丙酯作为侧链掺入。通过两种乙酸乙烯酯的水解，通过额外的分子内跨环醛醇缩合反应，获得具有四个连续立体中心的高度官能化的吲哚稠合双环[3.2.1]辛烷衍生物，作为单一区域异构体和非对映异构体。在上述两种改造的基础上，开发了一种经济的一锅三步级联反应。
For the first time, a gold-catalyzed [4+3] cycloaddition/C-H functionalization cascade was developed. This reaction provides efficient access to densely functionalized cyclohepta[b]indoles, in which a second propargylic ester is incorporated as a side chain, in excellent yields. By hydrolysis of the two vinyl acetates, highly functionalized indole-fused bicyclo[3.2.1]octane derivatives bearing four contiguous stereogenic centers were acquired as single regio- and diastereomers through an additional intramolecular transannular aldol reaction. On the basis of the above two transformations, an economical one-pot, three-step cascade reaction was developed.