Trimethylsilyl trifluoromethanesulfonate-promoted cycloaddition of nitrones with silyl enol ethers: synthesis and reactivity of 5-siloxyisoxazohdines
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 24,p. 3157-3165
- https://doi.org/10.1039/p19930003157
Abstract
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), the reaction of nitrones with silyl enol ethers affords 5-siloxyisoxazolidines under mild conditions, in good to excellent yields. 5-Siloxyisoxazolidines can undergo chemoselective reductions to Manoich bases or N-hydroxy-1,3-amino alcohols, and, in the presence of TMSOTf, react with silylated carbon nucleophiles at the acetalic C-5 carbon to give, for example, 5-allyl- and 5-cyano-isoxazolidines.Keywords
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