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Preparation of Fluoroalkenes via the Shapiro Reaction: Direct Access to Fluorinated Peptidomimetics

Ming-Hsiu Yang, Siddharth S. Matikonda and Ryan A. Altman*

*Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, United States, Email: raaltmanku.edu

M.-H. Yang, S. S. Matikonda, R. A. Altman, Org. Lett., 2013, 15, 3894-3897.

DOI: 10.1021/ol401637n (free Supporting Information)


Abstract

A Shapiro fluorination reaction enables a direct access to fluoroalkenes in good stereoselectivity 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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Key Words

Shapiro Reaction, Fluorination


ID: J54-Y2013