Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction): Scope and asymmetric applications
A vanadium-catalyzed method for the oxidation of prochiral aryl, allylic selenides with tandem 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.
Campbell Bourland,Carter, Rich G.,Yokochi, Alexandre F. T.
p. 1315 - 1329
(2007/10/03)
The first vanadium-catalyzed oxidation of aryl allylic selenides with in situ [2,3] sigmatropic rearrangement
The efficient synthesis of a series of 2°allylic alcohols from a vanadium-catalyzed oxidation of suitably disposed allylic selenides with tandem [2,3] sigmatropic rearrangement is outlined.
Carter,Bourland
p. 2031 - 2032
(2007/10/03)
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