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

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

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 deriv...

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Bibliographic Details
Main Authors: Liang, Xiaoyu, Guo, Pan, Yang, Wenjie, Li, Meng, Jiang, Chengzhou, Sun, Wangbin, Loh, Teck-Peng, Jiang, Yaojia
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Regioselective Synthesis
Annulation
Online Access:https://hdl.handle.net/10356/160880
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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