Methyl (2R)-2-tert-butyl-Δ4-1,3-oxazoline-3-carboxylate has been hydroformylated to give methyl (2R,4R)-2-tert-butyl-4-formyloxazolidine-3-carboxylate and methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate with up to 99% diastereoselectivities in homogeneous transition-metal-catalysed reactions. A mixture of regioisomers was formed in the presence of rhodium catalysts. Platinum catalysts gave almost exclusively methyl (2R,5S)-2-tert-butyl-5-formyl-oxazolidine-3-carboxylate. The formyl products obtained are important intermediates for the synthesis of homochiral amino acid derivatives of considerable synthetic value.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
- Materials Chemistry