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Issue 6, 1988
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Rhodium carbenoid mediated cyclisations. Part 2. Synthesis of cyclic ethers

Abstract

Alkylation of the dianion of methyl acetoacetate with the t-butyldimethylsilyl protected α,ω-halogeno alcohols (1)–(9) gives the β-keto esters (1) which are converted into the diazo alcohols (3) by diazo transfer and desilylation. Rhodium carbenoid cyclisation of the diazo alcohols (3bd) gives the 7-membered ethers (11)–(13) in good yield. The 8-membered ether (14) is formed in only modest yield from the diazo alcohol (3e), but cyclisation of the diazo alcohol (3f) to the 10-membered ether (15) was not successful.

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Article type: Paper
DOI: 10.1039/P19880001417
Citation: J. Chem. Soc., Perkin Trans. 1, 1988, 1417-1423
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    Rhodium carbenoid mediated cyclisations. Part 2. Synthesis of cyclic ethers

    J. C. Heslin and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1988, 1417
    DOI: 10.1039/P19880001417

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