Issue 13, 2020

Stereoselective synthesis of trifluoromethyl-substituted 2H-furan-amines from enaminones

Abstract

A straightforward strategy for synthesis of highly functionalized trifluoromethyl 2H-furans is described. The copper catalyzed method relies on a cascade cyclic reaction between enaminones and N-tosylhydrazones. This method allows the synthesis of 2-amino-3-trifluoromethyl-substituted 2H-furan derivatives carrying a quaternary stereogenic center as single diastereomers. The proposed reaction mechanism involves an amino-cyclopropane intermediate formed in the cyclopropanation of enaminones. The developed method tolerates a broad spectrum of functionalities, and the obtained 2H-furan derivatives are useful synthetic intermediates for preparing other trifluoromethyl-substituted compounds.

Graphical abstract: Stereoselective synthesis of trifluoromethyl-substituted 2H-furan-amines from enaminones

Supplementary files

Article information

Article type
Communication
Submitted
04 Nov 2019
Accepted
09 Jan 2020
First published
20 Jan 2020

Chem. Commun., 2020,56, 2043-2046

Stereoselective synthesis of trifluoromethyl-substituted 2H-furan-amines from enaminones

X. Liang, P. Guo, W. Yang, M. Li, C. Jiang, W. Sun, T. Loh and Y. Jiang, Chem. Commun., 2020, 56, 2043 DOI: 10.1039/C9CC08582C

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