Asymmetric 1,3-dipolar cycloaddition of nitrile oxides with optically active vinylboronic ester

Pinanyldioxy styrylboronic ester (1) was employed for asymmetric 1,3-dipolar cycloaddition with nitrile oxides, optically active △2-isoxazolines (3) or 4-hydroxy-△2-isoxazolines (4) were obtained. The effect of different bases on the selectivity of the cycloaddition reaction was studied.     

Asymmetric 1,3-dipolar cycloaddition of nitrile oxides to chiral acryloyl esters bearing glucofuranose as auxiliary

Asymmetric 1,3-dipolar cydoaddition of nitrite oxides to an acryloyl ester (1) derived from 1,2:5,6-di-O-isopropylidene glucose (6) was studied. Solvent and temperature effect was discussed. The single diastereoisomer was isolated with high diastereoselective excess.