ChemInform Abstract: Oxidative Conversion of Isoxazolidines to Isoxazolines.

✍ Scribed by P. LI; H.-J. GI; L. SUN; K. ZHAO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199824116

✦ Synopsis

Oxidative Conversion of Isoxazolidines to Isoxazolines. -The usual syntheses of isoxazolines often lead to diastereomeric mixtures of cycloadducts.

To circumvent this problem a method for the conversion of isoxazolidines into the corresponding isoxazolines is developed, which will retain the optical integrity gained in the synthesis of the starting material. The selective cleavage of the p-methoxybenzyl-N bond via DDQ oxidation is demonstrated as an unique case. This method might allow access to optically active isoxazolines, which are otherwise difficult to obtain. It is also successfully extended to the conversion of isoxazoline nucleoside analogues (V) into (VI), which can be further transformed by reported procedures to (VII). -(LI, P.; GI, H.-J.;