Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent

[GRAPHICS] Zinc-complexed methylene ammonium ylides are formed from tertiary amines and the Simmons-Smith reagent. These stable entities can be activated with n-BuLi to allow reactions typical of ammonium ylides such as [2,3] rearrangements. In the case of oxazolidine 12, ylide formation, activation, and subsequent [2,3] rearrangement was highly efficient and occurred with very high diastereoselectivity.