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Issue 27, 2019
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Diastereoselective synthesis of cyclopropanes bearing trifluoromethyl-substituted all-carbon quaternary centers from 2-trifluoromethyl-1,3-enynes beyond fluorine elimination

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Abstract

Herein, a one-pot, two-step procedure for the diastereoselective synthesis of cyclopropanes bearing trifluoromethyl-substituted all-carbon quaternary centers has been described. Trifluoromethyl-activated 1,3-enynes undergo cyclopropanation reactions with sulfur ylides under mild reaction conditions without fluoride elimination, which affords the cis-isomer mainly. Interestingly, a sequential TBAF-mediated deprotection of the triisopropylsilyl group results in a diastereoenriched epimerization which gives rise to the trans-cyclopropanes as the sole isomers.

Graphical abstract: Diastereoselective synthesis of cyclopropanes bearing trifluoromethyl-substituted all-carbon quaternary centers from 2-trifluoromethyl-1,3-enynes beyond fluorine elimination

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Article information


Submitted
28 Jan 2019
Accepted
18 Feb 2019
First published
18 Feb 2019

Chem. Commun., 2019,55, 3879-3882
Article type
Communication

Diastereoselective synthesis of cyclopropanes bearing trifluoromethyl-substituted all-carbon quaternary centers from 2-trifluoromethyl-1,3-enynes beyond fluorine elimination

S. Chen, J. Zhang, M. Yang, F. Liu, Z. Xie, Y. Liu, W. Lin, D. Wang, X. Li and J. Wang, Chem. Commun., 2019, 55, 3879
DOI: 10.1039/C9CC00785G

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