Radical cyclization on solid support: Synthesis of γ-butyrolactones
1999; Elsevier BV; Volume: 40; Issue: 17 Linguagem: Inglês
10.1016/s0040-4039(99)00503-1
ISSN1873-3581
AutoresYoshihiko Watanabe, Satoshi Ishikawa, Gou Takao, Takeshi Toru,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoSynthesis of γ-butyrolactones using radical cyclization on solid-phase has been achieved. Polymer-supported β-bromoethylacetals were treated with tributyltin hydride in the presence of a catalytic amount of α, α′-azobisisobutyronitrile to generate intermediate carbon radicals which cyclize onto the intramolecular carbon-carbon double bond. The cyclization products were released by Jones oxidation from resin to give γ-butyrolactones in good yields. Radical cyclization of bromoacetals on solid phase gave cyclic acetals which were cleaved from the solid phase by Jones oxidation to release γ-butyrolactones in good yields.Download : Download full-size image
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