Boron trifluoride etherate for regioselective rearrangement or opening of secondary aryl glycidic amides. (10th September 2022)

• Record Type: Journal Article
• Authors: Aparicio, David M.; Tépox-Luna, Dulce; Bedolla-Medrano, Mercedes; Gnecco, Dino; Juárez, Jorge R.; Mendoza, Ángel; Orea, María L.; Terán, Joel L.
• Is Part Of: Tetrahedron. Volume 122(2022)
• Publication Date: 2022-09-10
• Subjects: 1 aryl glycidic amides -- Keyword_2 α-formyl acid -- Keyword_3 α-ketoamides -- Keyword_4 fluorohydrin -- Keyword_5 boranuide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.132934
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A regioselective 1, 2-acyl, 1, 2-hydrogen migration, and intermolecular opening of secondary aryl glycidic amides catalyzed by BF3 ·OEt2 were investigated. Derived from this reaction, α-Formyl acid, α-ketoamides, or fluorohydrin derivatives could regioselective be obtained, depending on the nature of the aromatic ring substituent bearing on the oxirane ring. To demonstrate the plausible mechanism in the formation of α-formyl acid or alpha-keto amides derivatives, an isotopic labeling experiment was developed. Graphical abstract: Image 1