The terminal olefinic carbon of N-methacryloyl-2-oxazolidinones is smoothly acetalized by alcohols in the presence of PdClz catalyst. The use of 4 (S)-isopropyl-, phenyl-, and tert-butyl- 2-oxazolidinones as the chiral auxiliary resulted in the formation of the corresponding (2'SI- acetals in 61, 80, and 95% de, respectively. Reductive removal of the auxiliary with LiAIH4 followed by deacetalization produced (R)-3-hydroxy-2-methylpropanal. The enantiomer of ...
