Host: Division of Organic Chemistry, The Pharmaceutical Society of Japan
Pages 32-33
The inverse electron-demand 1,3-dipolar cycloaddition of nitrones with ynolate anions, followed by quenching with t-BuOH, produced substituted 5-isoxazolidinones with good trans-selectivity. These products were easily converted into β-amino acids via hydrogenation. Asymmetric 1,3-dipolar cycloaddition of ynolates with chiral nitrones derived from D-mannitol also successfully afforded the chiral products with high diastereoselectivity. These products, after separation of the minor isomers, were led to optically pure β-amino acids. These results show the first 1,3-dipolar cycloaddition and the first asymmetric reaction using ynolates.
