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Issue 9, 2004
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Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction): scope and asymmetric applications

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Abstract

A vanadium-catalyzed method for the oxidation of prochiral aryl, allylic selenides with tandem [2,3] sigmatropic rearrangement has been developed. This protocol has been screened on a series of substrates to test for its generality and effectiveness. The applicability of this methodology to the synthesis of enantiomerically enriched allylic alcohols has been studied on a series of chiral oxazole-containing systems with a diastereomeric ratio (d.r.) of up to 85 : 15. The chiral transfer observed in the allyl alcohol products is the result of a net 1,9- and/or 1,10-induction. Finally, the first example of a selenium–oxygen nonbonding interaction in oxazole-containing selenide appears to have been observed via X-ray crystal analysis.

Graphical abstract: Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction): scope and asymmetric applications

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Publication details

The article was received on 19 Dec 2003, accepted on 20 Feb 2004 and first published on 31 Mar 2004


Article type: Paper
DOI: 10.1039/B316502G
Citation: Org. Biomol. Chem., 2004,2, 1315-1329
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    Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction): scope and asymmetric applications

    T. C. Bourland, R. G. Carter and A. F. T. Yokochi, Org. Biomol. Chem., 2004, 2, 1315
    DOI: 10.1039/B316502G

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