Treatment of optically active epoxyurethanes with four contiguous stereogenic centres [derived from a kinetic resolution during Sharpless epoxidation of diphenylphosphinoyl (Ph2PO) allylic alcohols] with base leads to sequential regioselective intramolecular nucleophilic attack (on the epoxide) and Horner-Wittig elimination to give single geometrical isomers of alkenyl oxazolidinones. Any stereoisomer of 4-alkenyloxazolidin-2-ones containing 1,4-related stereogenic centres spanning a double bond of either geometry can be produced with control over geometrical (E,Z), relative (syn,anti) and absolute (R,S) stereochemistry.
|Number of pages||9|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 7 Sep 1998|