Stereoselective synthesis of novel 4,5-epoxy-1,2-oxazin-6-ones and alpha,beta-epoxy-gamma-amino acids from beta-lithiated oxazolinyloxiranes and nitrones.
[reaction: see text] A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5]decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-gamma-amino acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.
Capriati
Vito
V
Dipartimento Farmaco-Chimico, Università di Bari, C.N.R, Bari, Italy.
Degennaro
Leonardo
L
Florio
Saverio
S
Luisi
Renzo
R
Punzi
Pasqualina
P
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D004852:Epoxy Compounds; D009589:Nitrogen Oxides; D010078:Oxazines; D010080:Oxazoles; C015388:nitrones; D008094:Lithium