Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

Article abstract of DOI:10.1016/S0040-4039(00)60383-0

Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereo specifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.