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Synfacts 2009(9): 0964-0964  
DOI: 10.1055/s-0029-1217772
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 4,4-Difluorodihydrofuran-3(2H)-ones

Contributor(s): Victor Snieckus, Johnathan Board
M. Schuler, A. Monney, V. Gouverneur*
Chemistry Research Laboratory, Oxford, UK
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

Reported is the synthesis of 4,4-difluorodihydrofuran-3(2H)-ones through a phosphine-catalyzed cyclization of β-hydroxy-α,α-difluoroynones. The starting ynones were synthesized using the well-established Reformatsky reaction. The reaction is highly selective for the Z-isomer, as shown by NOE experiments on the alcohol derivatives, produced by l-Selectride reduction of the furanones. A plausible catalytic cycle was proposed without evidence.