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Article Dans Une Revue Organic Letters Année : 2016

Access to Constrained Fluoropseudopeptides via Ring-Closing-Metathesis of Fluoroalkenes

Résumé

Bis-alkene substrates, containing one fluoroalkene and linked by an amide moiety, have been designed and synthesized to be subjected to ring-closing metathesis reactions. The substitution of fluoroalkene by a phenyl group enhanced the reactivity, and the resulting fluorinated lactams were obtained in high yields except when a hindered alkyl group was present in the molecule. The cycles were then subjected to ring opening in order to develop a new route toconstrained fluoropseudopeptides bearing a fluoroalkene as a peptide bond mimic.
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Dates et versions

hal-01404830 , version 1 (29-11-2016)

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David Guérin, Isabelle Dez, Annie-Claude Gaumont, Xavier Pannecoucke, Samuel Couve-Bonnaire. Access to Constrained Fluoropseudopeptides via Ring-Closing-Metathesis of Fluoroalkenes. Organic Letters, 2016, 18 (15), pp.3606-3609. ⟨10.1021/acs.orglett.6b01631⟩. ⟨hal-01404830⟩
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