Stereoselective Synthesis of Trifluoromethylsubstituted 2H-furan-amines from Enaminones

Xiaoyu Liang,^a Pan Guo,^a Wenjie Yang,^a Meng Li,^a Chengzhou Jiang,^a Wangbin Sun,^a Teck-Peng Loh ^*ab and Yaojia Jiang^*a

^a Institute of Advanced Synthesis, Nanjing Tech University, Nanjing 211816, P. R. China.

^b Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 637616, Singapore.

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 trifluoromethylsubstituted compounds.

Chem. Commun. DOI: 10.1039/c9cc08582c (2019年影响因子:6.164)

文章链接：https://pubs.rsc.org/en/content/articlelanding/2020/CC/C9CC08582C#!divAbstract