A Rapid Entry to Diverse γ-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived γ-Lactones and Metal-Catalyzed Postfunctionalization
2015; Wiley; Volume: 2015; Issue: 28 Linguagem: Inglês
10.1002/ejoc.201500663
ISSN1434-193X
AutoresNicolas Chopin, Hikaru Yanai, Shinya Iikawa, Guillaume Pilet, Jean‐Philippe Bouillon, Maurice Médebielle,
Tópico(s)Chemical Synthesis and Analysis
ResumoThe synthesis of a series of diverse methyl and benzyl γ-ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two- or three-step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ-ylidenetetronates occurred under mild conditions to provide the corresponding C-3-brominated γ-unsaturated lactones. Di- and tribrominated γ-lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki–Miyaura, and Sonogashira cross-coupling reactions to yield functionalized methyl and benzyl γ-ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross-coupling reactions were desilylated and converted into 1,2,3-triazole derivatives through a copper(I)-catalyzed 1,3-dipolar cycloaddition reaction with benzyl azide.
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