2,3-Wittig rearrangement

The [2,3]-Wittig rearrangement is the transformation of an allylic ether into a homoallylic alcohol via a concerted, pericyclic process. Because the reaction is concerted, it exhibits a high degree of stereocontrol, and can be employed early in a synthetic route to establish stereochemistry. The Wittig rearrangement requires strongly basic conditions, however, as a carbanion intermediate is essential. [1,2]-Wittig rearrangement is a competitive process.[1]

  1. ^ Nakai, T.; Mikami, K. (2004). "The [2,3]-Wittig Rearrangement". Organic Reactions. doi:10.1002/0471264180.or046.02. ISBN 0471264180.