716368-89-7Relevant academic research and scientific papers
Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction): Scope and asymmetric applications
Campbell Bourland,Carter, Rich G.,Yokochi, Alexandre F. T.
, p. 1315 - 1329 (2007/10/03)
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.
