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Issue 66, 2015
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Diastereoselective Johnson–Corey–Chaykovsky trifluoroethylidenation

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Abstract

(2,2,2-Trifluoroethyl)diphenylsulfonium triflate was found to be an efficient ylide reagent for the Johnson–Corey–Chaykovsky reaction to afford trifluoromethyl epoxides, cyclopropanes and aziridines. Interestingly, excellent but different diastereoselectivity was observed for these transformations. Both trifluoromethyl epoxides and cyclopropanes were obtained with trans-selectivity, whereas aziridines were obtained with cis-selectivity.

Graphical abstract: Diastereoselective Johnson–Corey–Chaykovsky trifluoroethylidenation

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Publication details

The article was received on 17 Jun 2015, accepted on 06 Jul 2015 and first published on 06 Jul 2015


Article type: Communication
DOI: 10.1039/C5CC04991A
Citation: Chem. Commun., 2015,51, 13127-13130

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    Diastereoselective Johnson–Corey–Chaykovsky trifluoroethylidenation

    Y. Duan, B. Zhou, J. Lin and J. Xiao, Chem. Commun., 2015, 51, 13127
    DOI: 10.1039/C5CC04991A

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