Diastereoselective synthesis of alpha-methyl and alpha-hydroxy-beta-amino acids via 4-substituted-1,3-oxazinan-6-ones.
1,3-oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.
Sleebs
Brad E
BE
Department of Chemistry, La Trobe University, Bundoora, Victoria 3086, Australia.
Hughes
Andrew B
AB
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D006868:Hydrolysis; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D010078:Oxazines