Organic letters

Preparation of fluoroalkenes via the shapiro reaction: direct access to fluorinated peptidomimetics

MH Yang, SS Matikonda, RA Altman

Index: Yang, Ming-Hsiu; Matikonda, Siddharth S.; Altman, Ryan A. Organic Letters, 2013 , vol. 15, # 15 p. 3894 - 3897

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Citation Number: 18

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 ...