Synthesis and reactivity of Z and E functionalized allylic fluorides |
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| Authors: | Michaël PrakeschDanielle Grée René Grée |
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| Institution: | ENSCR, Laboratoire de Synthèses et Activations de Biomolécules, CNRS UMR 6052, Avenue du Général Leclerc, 35700 Rennes, France |
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| Abstract: | The allylic fluorides 1 and 2 are used as models to study the effect of the allylic C-F bond on the diastereoselectivity of reactions occurring on the vicinal double bond, as well as the compatibility of this C-F bond with various reagents. The configurational stability of the Z double bonds in enals and enones 1 and 3 is noteworthy. This allowed us to perform various types of reactions (including thermal Diels-Alder cycloadditions) on derivatives 1 with full control of the Z geometry. |
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| Keywords: | fluorine allylic fluoride enone enal |
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