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供体/受体铑(II)氮杂乙烯基卡宾的形式烯丙基化和对映选择性环丙烷化

Formal Allylation and Enantioselective Cyclopropanation of Donor/Acceptor Rhodium(II) Azavinyl Carbenes.

作者信息

Liu Zhili, Chen Lianfen, Zhu Dong, Zhu Shifa

机构信息

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.

State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China.

出版信息

Org Lett. 2021 Feb 19;23(4):1275-1279. doi: 10.1021/acs.orglett.0c04251. Epub 2021 Feb 3.

Abstract

A highly efficient formal allylation of dihydronaphthotriazoles with alkenes under rhodium(II) catalysis is reported. Various allyl dihydronaphthalene derivatives were furnished via rhodium(II) azavinyl carbenes with moderate to good yields and excellent chemoselectivity. When monosubstituted alkenes are used, cyclopropanation occurs and good to excellent enantioselectivities have been achieved. Particularly noteworthy is the allylic C(sp)-H activation instead of traditional C(sp)-H activation in the formal allylation process.

摘要

据报道,在铑(II)催化下,二氢萘并三唑与烯烃可进行高效的形式烯丙基化反应。通过铑(II)氮杂乙烯基卡宾可制备各种烯丙基二氢萘衍生物,产率中等至良好,化学选择性优异。当使用单取代烯烃时,会发生环丙烷化反应,并实现了良好至优异的对映选择性。特别值得注意的是,在形式烯丙基化过程中发生的是烯丙基C(sp)-H活化,而非传统的C(sp)-H活化。

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