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Synfacts 2010(8): 0875-0875  
DOI: 10.1055/s-0030-1257847
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

A Lactonization Route to 5-(Trifluoromethyl)-2(5H)-furanones

Contributor(s): Victor Snieckus, Wei Gan
A. B. Koldobskii, N. P. Tsvetkov, E. V. Solodova, V. N. Kalinin
Russian Academy of Sciences, Moscow, Russian Federation
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Reported is a three-step synthesis of 5-trifluoromethylated furanones from cyclo­butenes. The starting materials are available via a [2+2] cyclization from the corresponding halogenated trifluoroacetylacetylenes with primary alkenes. Other [2+2] and [2+4] cycloadducts A and B have been found to construct analogous furanones C and D, although the process suffers from luck of diastereoselectivity. Interestingly, γ-hydroxy acids E were found to be extremely ­resistant to lactonization under thermal or DCC-promoted conditions and required excess trifluoroacetic anhydride.