DOI: 10.1039/C9CC08582C
ChemComm
Carrillo, E. Reyes, T. Tejero, P. Merino and J. L. Vicario, Angew.
Chem., Int. Ed., 2018, 57, 8225-8229.
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access to a variety of compounds housing an all-carbon
stereogenic center with a CF3 group.
In summary, we have demonstrated an efficient and practical
approach to prepare highly functionalized 2-amino-3-
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5
trifluoromethyl-substituted 2H-furan derivatives with
quaternary all-carbon stereogenic center as single diastereomers.
The reaction proceeds via cascade cyclization between
a
70 8
a
enaminones and N-tosylhydrazones and employs a cheap copper
catalyst under basic conditions. We believe the reaction involves
10 an initial formation of an amino-cyclopropane intermediate,
which undergoes selective C-C bond cleavage. The method
tolerates a broad spectrum of functionalities, and the obtained
2H-furan derivatives can be further applied to prepare unique
trifluoromethyl-substituted compounds.
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15 Acknowledgement
The authors gratefully acknowledge funding from the
National Natural Science Foundation of China (21971112),
Jiangsu Province Funds Surface Project (BK 20161541) and
the Starting Funding of Research (39837107) from Nanjing
20 Tech University. Dr. Li Yongxing (NTU) is thanked for single
crystal X-ray diffraction analysis. Dr. Juha Siitonen and Mr.
Stephen Chamness (Rice University) are thanked for
proofreading the manuscript.
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