Camiletti, Chiara ; Dhavale, Dilip D. ; Gentiluccia, Luca ; Trombini, Claudio (1993) Trimethylsilyl trifluoromethanesulfonate-promoted cycloaddition of nitrones with silyl enol ethers: synthesis and reactivity of 5-siloxyisoxazolidines Journal of the Chemical Society, Perkin Transactions 1 (24). pp. 3157-3165. ISSN 0300-922X
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Official URL: http://pubs.rsc.org/en/content/articlelanding/1993...
Related URL: http://dx.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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 87240 |
| Deposited On: | 16 Mar 2012 06:13 |
| Last Modified: | 19 Mar 2012 10:46 |
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