Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization

…, E Leclerc, JC Quirion, X Pannecoucke

Index: Fourrire, Gaelle; Leclerc, Eric; Quirion, Jean-Charles; Pannecoucke, Xavier Journal of Fluorine Chemistry, 2012 , vol. 134, p. 172 - 179

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Abstract

The synthesis of polyhydroxylated 1, 1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1, 5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A ...

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