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Regiocontrolled fluorination of 2-hydroxyalkyl dihydropyrans and carbonyl derivatives |
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| Authors: | Nguyen Quang VuDanielle Grée René GréeEric Brown Gilles Dujardin |
| Institution: | a Laboratoire de Synthèse Organique, UMR CNRS 6011, Université du Maine, F-72085, Le Mans Cedex-9, France b ENSCR, Laboratoire de Synthèses et Activations de Biomolécules UMR CNRS 6052, Avenue du général Leclerc, F-35700 Rennes, France |
| Abstract: | Reaction of polysubstituted 2-hydroxyalkyldihydropyrans with DAST led regiospecifically to fluorination at the exocyclic position, except for primary alcohols. Difluorination of carbonylated analogues with deoxo-fluor™ occurred also regioselectively. The unexpected stability and synthetic potential of these new allylic fluorides are discussed. |
| Keywords: | fluorination DAST deoxo-fluor&trade dihydropyran C-glycoside |
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