Tetrahedron letters

Intramolecular Free Radical Cyclisations onto Vinyl Ethers. A Method for the Synthesis of β-oxy-γ-butyrolactones

M Ladlow, G Pattenden

Index: Ladlow, Mark; Pattenden, Gerald Tetrahedron Letters, 1984 , vol. 25, # 38 p. 4317 - 4320

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Citation Number: 60

Abstract

Radical cyclisation of the vinyl ether bromides (2) and (7) in the presence of tri-n-butylstannane produces precursors [ (3) and (8)] to the β-oxy-γ-butyrolactones (6) and (9) in high yields (80°). By contrast, treatment of (2) and (7) with -(dimethylglyoximato)(pyridine)cobalt(I) chloride followed by oxidation of the intermediates (5) and (11) led to the corresponding β-oxy-γ-butyrolactones (4) and (12) respectively. ... All new compounds showed satisfactory spectral data and ...