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金催化实现呋喃稠合环丁烯作为交叉环加成反应的平台。

Gold Catalysis Enabling Furan-Fused Cyclobutenes as a Platform toward Cross Cycloadditions.

机构信息

Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. China.

College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, People's Republic of China.

出版信息

Org Lett. 2021 May 7;23(9):3701-3705. doi: 10.1021/acs.orglett.1c01079. Epub 2021 Apr 27.

Abstract

The inherently strained furan-fused cyclobutenes, generated via cycloisomerizations of allenyl ketones bearing cyclopropyl moiety under gold catalysis, have been utilized as reactive building blocks toward cross cycloadditions. The [4 + 2] and [3 + 2] annulations of these species with benzo[]isoxazoles and -iminoquinazolinium ylides furnish various three-dimensional cyclobutane-bridged polyheterocycles in good yields. A wide range of typically electron-deficient 1,3-dienes, heterodienes, and 1,3-dipoles can trap furan-fused cyclobutenes to afford several polycyclic architectures.

摘要

在金催化下,带有环丙基部分的烯丙基酮的环异构化生成了固有张力的呋喃稠合环丁烯,它们被用作反应性构建块进行交叉环加成反应。这些物质与苯并[]异恶唑和-亚氨基喹唑啉鎓叶立德的[4+2]和[3+2]环加成反应以高产率提供了各种具有三维环丁烷桥的多杂环。广泛的典型缺电子 1,3-二烯、杂二烯和 1,3-偶极子可以捕获呋喃稠合环丁烯,得到几种多环结构。

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