Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides

Chengwen Li; Yilin Zhao; Jiaxin Zhou; Xue Wang; Jingli Hou; Yuguang Song; Wenjuan Liu; Guifang Han

doi:10.1039/D0OB01833C

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides†

Chengwen Li,^a Yilin Zhao,^a Jiaxin Zhou,^a Xue Wang,^a Jingli Hou,

^a Yuguang Song,

^a Wenjuan Liu^b and Guifang Han

*^a

Author affiliations

* Corresponding authors

^a Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin 300070, P. R. China
E-mail: hanguifang@tmu.edu.cn

^b Jiangsu Duxingzhiyuan New Material Technology Co. Ltd, Nantong, P. R. China

Abstract

An efficient method for the synthesis of difluoroalkylated 2-azaspiro[4.5]decanes via copper-catalyzed difluoroalkylation of N-benzylacrylamides with ethyl bromodifluoroacetate has been established. The reaction experienced a tandem radical addition and dearomatizing cyclization process. In addition, the resultant products can be smoothly converted into a difluoroalkylated quinolinone and saturated spirocyclohexanone scaffold.

This article is part of the themed collections: Synthetic methodology in OBC and Catalysis & biocatalysis in OBC

Download options Please wait...

Supplementary files

Supplementary information PDF (4247K)

Article information

DOI: https://doi.org/10.1039/D0OB01833C
Article type: Communication
Submitted: 05 Sep 2020
Accepted: 12 Oct 2020
First published: 12 Oct 2020

Download Citation

Org. Biomol. Chem., 2020,18, 8376-8380

Permissions

Request permissions

Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides

C. Li, Y. Zhao, J. Zhou, X. Wang, J. Hou, Y. Song, W. Liu and G. Han, Org. Biomol. Chem., 2020, 18, 8376 DOI: 10.1039/D0OB01833C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides

Social activity

Search articles by author

Spotlight

Advertisements