Mp. Sibi et al., A NEW ELECTROPHILIC ALANINOL SYNTHON - A GENERAL-ROUTE TO OXAZOLIDINONES OF D-2-AMINO OR (R)-2-AMINO ALCOHOLS FROM L-SERINE, Journal of the Chemical Society. Perkin transactions. I, (13), 1994, pp. 1675-1678
A new electrophilic alaninol synthon, (S)-4-(4'-tolylsulfonyloxymethyl
) oxazolidin-2-one, derived from serine, undergoes nucleophilic displa
cements with Gilman cuprates and/or Grignard/CuX reagents in high yiel
d to provide (R)-4-substituted oxazolidinones.