Issue 24, 1993

Trimethylsilyl trifluoromethanesulfonate-promoted cycloaddition of nitrones with silyl enol ethers: synthesis and reactivity of 5-siloxyisoxazohdines

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 3157-3165

Trimethylsilyl trifluoromethanesulfonate-promoted cycloaddition of nitrones with silyl enol ethers: synthesis and reactivity of 5-siloxyisoxazohdines

C. Camiletti, D. D. Dhavale, L. Gentiluccia and C. Trombini, J. Chem. Soc., Perkin Trans. 1, 1993, 3157 DOI: 10.1039/P19930003157

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements