4.8 Article

Synthesis of β-Fluoro-α,β-Unsaturated Amides from the Fragmentation of Morpholine 3,3,3-Trifluoropropanamide by Grignard Reagents

Journal

ORGANIC LETTERS
Volume 22, Issue 7, Pages 2630-2633

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00599

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Funding

  1. University of Mississippi
  2. National Institute of Drug Abuse [R15DA046795]

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Fluoroalkenes serve as bioisosteres to peptide bonds and are resistant to hydrolytic enzymes in vivo. Currently, alpha-fluoro-alpha,beta-unsaturated carbonyl compounds are readily accessible via general synthetic methods; however, beta-fluoro-alpha,beta-unsaturated carbonyl groups are more challenging to construct. To address this need, we have designed a reagent, morpholine 3,3,3-trifluoropropanamide, that creates (E)-beta-fluoro-alpha,beta-unsaturated amides upon the addition of many commonly used Grignard reagents. Reactions with this reagent enable a high level of stereocontrol in the fluoroalkene product.

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