Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids.
Highly diastereoselective and enantioselective addition of N-benzylhydroxylamine to imides 17 and 20-30 produces alpha,beta-trans-disubstituted N-benzylisoxazolidinones 19 and 31-41. These reactions proceed in 60-96% ee with 93-99% de's using 5 mol % of Mg(NTf2)2 and ligand 18. The product isoxazolidinones can be hydrogenolyzed directly to provide alpha,beta-disubstituted-beta-amino acids.
D000596:Amino Acids / Q000138:chemical synthesis*; D006898:Hydroxylamines / Q000737:chemistry; D007094:Imides / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D006898:Hydroxylamines; D007094:Imides; D007555:Isoxazoles