A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.
- ammonium ylide
- oxazolidinyl group
- [2,3]-sigmatropic rearrangement
- α-Amino ketones