Oxazolinyloxiranyllithium-mediated stereoselective synthesis of alpha-epoxy-beta-amino acids.
[reaction: see text] The stereoselective synthesis of novel alpha-epoxy-beta-amino acids is described by a route that combines the chemistry of oxazolinyloxiranyllithiums with that of nitrones. The intermediate trioxadiazadispiro[2.0.4.3]undecanes 4 have been isolated and converted by hydrolysis into epoxy-5-isoxazolidinones 5 which can be transformed into the alpha-epoxy-beta-amino acids 8 by N-O reduction.
Luisi
Renzo
R
Dipartimento Farmaco-Chimico, Università di Bari, Via E. Orabona 4, I-70126 Bari, C.N.R., Istituto di Chimica dei Composti OrganoMetallici ICCOM, Sezione di Bari, Italy.
Capriati
Vito
V
Degennaro
Leonardo
L
Florio
Saverio
S
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000596:Amino Acids; D004852:Epoxy Compounds; D009589:Nitrogen Oxides; D009942:Organometallic Compounds; D023303:Oxazolidinones; D008094:Lithium