New Chiral Ortho-P,S-Difunctionalized Aromatic Compounds

Abstract

A new method to prepare enantioenriched sulfinates was developed to obtain optically active ortho-methylsulfinyl(phenylphosphonates). It consists of a diastereoselective oxidation of sulfenates to sulfinates. Additionally, preliminary results concerning the synthesis of ortho-phophonylated benzylic thiol derivatives via a new P═S to P═C [1,4]-rearrangement and a first synthetic application of these compounds are also described.

Acknowledgments

This work was performed with the support of the EC within the Vth framework program (Contract ICA-CT-2000-70021-Centre of Excellence) of the French CNRS and the Polish Academy of Sciences.

Notes

^a Crude product with satisfactory purity.

^b Purified product by column chromatography.

Usually, sulfanyl chlorides are unstable compounds, decomposing easily to disulfides.