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Issue 2, 2001
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Juliá–Colonna stereoselective epoxidation of some α,β-unsaturated enones possessing a stereogenic centre at the γ-position: synthesis of a protected galactonic acid derivative

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Abstract

The oxidation of enones 6–8 using peroxide or percarbonate and polyleucines as catalysts gave the corresponding diastereomers 9–12 in high yield. The compound 9 was converted into the galactonic acid derivative 16 in five steps and in an overall yield of nearly 60%. Polyleucines are shown to be catalysts powerful enough to overturn the intrinsic stereocontrol in the chosen substrates.

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Article information


Submitted
01 Sep 2000
Accepted
10 Nov 2000
First published
18 Dec 2000

J. Chem. Soc., Perkin Trans. 1, 2001, 149-153
Article type
Paper

Juliá–Colonna stereoselective epoxidation of some α,β-unsaturated enones possessing a stereogenic centre at the γ-position: synthesis of a protected galactonic acid derivative

P. C. Ray and S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 2001, 149 DOI: 10.1039/B007100P

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