Mislow-Evans sigmatropic rearrangement reaction

An allylic halogen oxide [2,3]-sigmatropic rearrangement is another intriguing analogue of the Mislow-Evans process. In this scenario tScheme 1R.7QT oxidation of an allylic iodide provides iodoso intermediate 282, which rearranges to the corresponding allylic hypoiodite 283. Yamamoto et al. found that the reaction worked best with excess peracid oxidant, as the initially formed hypoiodite was further oxidized to the iodate ester (284), an intermediate... 

What do we mean by transfer of chirality Reactions in which the stereoselective formation of one stereogenic center is connected to the destruction of another stereogenic center involve transfer of chirality. Sigmatropic rearrangements are a large family of intramolecular reactions that often can be used to transfer chirality. We will look at two examples (1) the Claisen rearrangement (of allyl vinyl ethers to j8,7-unsaturated carbonyl compounds) and (2) the Mislow-Evans rearrangement (of allylic sulfoxides to allylic alcohols via sulfenate esters). 

---