Anionic inverse electron-demand 1,3-dipolar cycloaddition of nitrones with ynolates. Facile stereoselective synthesis of 5-isoxazolidinones leading to beta-amino acids.
[reaction: see text] The inverse electron-demand 1,3-dipolar cycloaddition of nitrones with ynolates, followed by quenching with t-BuOH, produced substituted 5-isoxazolidinones with good trans-selectivity. These products were easily converted into beta-amino acids.
Shindo
Mitsuru
M
Institute for Medicinal Resources, University of Tokushima, Sho-machi 1, Japan. shindo@ph2.tokushima-u.ac.jp
Itoh
Kotaro
K
Tsuchiya
Chinatsu
C
Shishido
Kozo
K
D000480:Alkynes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis*; D000838:Anions / Q000737:chemistry; D004583:Electrons; D009589:Nitrogen Oxides / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000480:Alkynes; D000596:Amino Acids; D000838:Anions; D009589:Nitrogen Oxides; D023303:Oxazolidinones; C015388:nitrones