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

• 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
• Institution: Nanyang Technological University

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.