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Issue 38, 2013
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A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF3SiMe3 as a trifluoromethylating agent

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Abstract

A general synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones is described. The fluoride-catalyzed nucleophilic addition of a trifluoromethyl (CF3) group generated from (trifluoromethyl)trimethylsilane (CF3SiMe3, Ruppert–Prakash reagent) to a masked maleic anhydride 1 (cyclopentadienemaleic anhydride adduct) provides the corresponding adducts 2 with high stereoselectivity. The γ-trifluoromethyl α,β-unsaturated γ-butyrolactones 4 were obtained after treatment of the adducts 2 with Grignard reagents, followed by flash-vacuum pyrolysis.

Graphical abstract: A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF3SiMe3 as a trifluoromethylating agent

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Publication details

The article was received on 17 Jun 2013, accepted on 31 Jul 2013 and first published on 01 Aug 2013


Article type: Paper
DOI: 10.1039/C3OB41247D
Citation: Org. Biomol. Chem., 2013,11, 6650-6658
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    A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF3SiMe3 as a trifluoromethylating agent

    C. Masusai, D. Soorukram, C. Kuhakarn, P. Tuchinda, C. Pakawatchai, S. Saithong, V. Reutrakul and M. Pohmakotr, Org. Biomol. Chem., 2013, 11, 6650
    DOI: 10.1039/C3OB41247D

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