Tetrahedron Letters p. 3411 - 3414 (1999)
Update date:2022-08-02
Topics:
Watanabe, Yoshihiko
Ishikawa, Satoshi
Takao, Gou
Toru, Takeshi
Synthesis 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.
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