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Preparation of fluoroalkenes via the Shapiro reaction: direct access to fluorinated peptidomimetics
Ming-Hsiu Yang1, Siddharth S Matikonda, Ryan A Altman
1Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, USA.
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.
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