由 Grignard 试剂断裂吗啉 3,3,3-三氟丙酰胺合成β-氟-α,β-不饱和酰胺。
Synthesis of β-Fluoro-α,β-Unsaturated Amides from the Fragmentation of Morpholine 3,3,3-Trifluoropropanamide by Grignard Reagents.
机构信息
Department of BioMolecular Sciences, University of Mississippi, University, Mississippi 38677, United States.
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
出版信息
Org Lett. 2020 Apr 3;22(7):2630-2633. doi: 10.1021/acs.orglett.0c00599. Epub 2020 Mar 17.
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.
摘要
氟代烯烃可用作肽键的生物等排体，并且在体内抵抗水解酶。目前，α-氟-α，β-不饱和羰基化合物可以通过一般的合成方法轻松获得；但是，β-氟-α，β-不饱和羰基基团的构建更具挑战性。为了满足这一需求，我们设计了一种试剂，即吗啉 3,3,3-三氟丙酰胺，当添加许多常用的格氏试剂时，该试剂会生成（）-β-氟-α，β-不饱和酰胺。该试剂的反应使氟代烯烃产物具有高水平的立体控制。
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