Synthesis of chiral 2-oxo- and 2-thio-1,3,2-oxazaphospholidines via the asymmetric cyclization of l-serinoates with (thio)phosphoryl dichlorides

Abstract

In this article, we have described the asymmetric cyclization of L‐serinoates and N‐benzyl L‐serinoate with phosphoro(no‐)dichloridates or their thio‐analog, respectively, and we have investigated the asymmetric induction effect of the chiral carbon center on the forming of a chiral phosphorus center. The diastereomeric excess percentages (de%) of the desired products 2‐oxo‐ and 2‐thio‐1,3,2‐oxazaphospholidines, are obtained based on their 31P NMR data. In some cases, the cyclization products have been separated as pure diastereomers by column chromatography. Their configuration is preliminarily discussed. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:187–191, 2000