StereoselectiveSynthesis ofTrifluoromethylsubstituted2H-furan-amines fromEnaminones

Xiaoyu Liang,^aPan Guo,^aWenjie Yang,^aMeng Li,^aChengzhou Jiang,^aWangbin Sun,^aTeck-Peng Loh^*aband Yaojia Jiang^*a

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

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

Abstract:A straightforward strategy for synthesis of highly functionalizedtrifluoromethyl2H-furans is described. The copper catalyzedmethod relies on a cascade cyclic reaction between enaminonesandN-tosylhydrazones. This method allows the synthesis of 2-amino-3-trifluoromethyl-substituted2H-furan derivatives carrying a quaternarystereogenic center as single diastereomers. The proposed reactionmechanism involves an amino-cyclopropane intermediate formed inthe cyclopropanation of enaminones. The developed method tolerates abroad spectrum of functionalities, and the obtained2H-furan derivativesare 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