Optically active tricarbonyl(η 6 -o-trimethylsilylbenzaldehyde)chromium( O ) complexes in organic synthesis: a highly diastereoselective 1,3-dipolar cycloaddition with electron-rich olefins
Authors:
- Chisato MukaiCMChisato Mukai
- In Jong KimIKIn Jong Kim
- Won Jea ChoWCWon Jea Cho
- Masaru KidoMKMasaru Kido
- Miyoji HanaokaMHMiyoji Hanaoka
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 20,p. 2495-2503
Abstract
Heating of a racemic nitrone 2, derived from tricarbonyl(η6-o-trimethylsilylbenzaldehyde)chromium(o) complex 1, with electron-rich olefins gave after decomplexation the cis-3,5-disubstituted isooxazolidines in a highly stereo- and regio-selective manner. Similarly, high selectivities were observed when the nitrone 9 possessing no silyl group at the ortho position on its benzene ring was employed instead of 2. The corresponding non-complexed nitrones were found to provide the cis-isoxazolidines in a moderately selective fashion or the trans-ones predominantly. Treatment of chiral 2 with electron-rich olefins afforded the corresponding chiral cis-3,5-disubstituted isoxazolidines exclusively. The enantiomeric excess for cycloadducts thus obtained was determined to be 96- > 98%. The absolute configuration of these optically active isoxazolidine derivatives was established on the basis of an X-ray crystallographic analysis.Keywords
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