Rhodium carbenoid mediated cyclisations. Part 2. Synthesis of cyclic ethers
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1417-1423
- https://doi.org/10.1039/p19880001417
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 (3b–d) 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.Keywords
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