title: Preparation of fluoroalkenes via the Shapiro reaction: direct access to fluorinated peptidomimetics.
abstract: Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.
authors.affiliation: Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, USA.
authors.forename: Ming-Hsiu
authors.initials: MH
authors.lastname: Yang
authors.forename: Siddharth S
authors.initials: SS
authors.lastname: Matikonda
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Altman
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D057786:Peptidomimetics; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006845:Hydrocarbons, Fluorinated; D057786:Peptidomimetics