Regioselective bromination of tetronic acid-derived c-lactones and metal-catalyzed post-functionalization: an efficient access to new c-ylidenetetronate derivatives

Shinya Likawa (1) , Nicolas Chopin , Guillaume Pilet (2) , J.-P. Bouillon (3) , Maurice Médebielle (1)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 LMI - Laboratoire des Multimatériaux et Interfaces
3 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The synthesis of several methyl and benzyl c-ylidenetetronates was accomplished and the bromination reactions of these derivatives, using bromine or N-bromosuccinimide (NBS), were found to occur under mild conditions. Several new brominated c-unsaturated lactones derived from tetronic acid were prepared in moderate to good yields, with some of them characterized by single crystal X-ray diffraction. A preliminary reactivity study of two bromine-derived c-benzylidene methyl tetronates, in Sonogashira cross-coupling reactions, with also preparation of 1,2,3-triazole-derived c-benzylidene methyl tetronate under Cu(I)-catalyzed condition, was performed with an indication that these brominated c-benzylidene tetronates are useful platforms to produce diversified c-lactones.

Domaines: Chimie organique

Shinya Likawa, Nicolas Chopin, Guillaume Pilet, J.-P. Bouillon, Maurice Médebielle. Regioselective bromination of tetronic acid-derived c-lactones and metal-catalyzed post-functionalization: an efficient access to new c-ylidenetetronate derivatives. Tetrahedron Letters, 2013, pp.4577-4581. ⟨10.1016/j.tetlet.2013.06.106⟩. ⟨hal-01015236⟩