"Synthesis of β-Fluoro-α,β-Unsaturated Amides from the Fragmentation of" by Amna T. Adam, Frank R. Fronczek et al.

Faculty Publications

Title

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

Authors

Amna T. Adam, Department of BioMolecular Sciences, University of Mississippi, University, Mississippi 38677, United States.
Frank R. Fronczek, Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
David A. Colby, Department of BioMolecular Sciences, University of Mississippi, University, Mississippi 38677, United States.

Document Type

Article

Publication Date

4-3-2020

Abstract

Fluoroalkenes serve as bioisosteres to peptide bonds and are resistant to hydrolytic enzymes in vivo. Currently, α-fluoro-α,β-unsaturated carbonyl compounds are readily accessible via general synthetic methods; however, β-fluoro-α,β-unsaturated carbonyl groups are more challenging to construct. To address this need, we have designed a reagent, morpholine 3,3,3-trifluoropropanamide, that creates ()-β-fluoro-α,β-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.

Publication Source (Journal or Book title)

Organic letters

First Page

2630

Last Page

2633

Recommended Citation

Adam, A. T., Fronczek, F. R., & Colby, D. A. (2020). Synthesis of β-Fluoro-α,β-Unsaturated Amides from the Fragmentation of Morpholine 3,3,3-Trifluoropropanamide by Grignard Reagents. Organic letters, 22 (7), 2630-2633. https://doi.org/10.1021/acs.orglett.0c00599

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