872359-36-9Relevant academic research and scientific papers
Asymmetric oxidation of sulfenates to sulfinates as a new route to optically active ortho-phosphorylated phenyl sulfoxides
Hamel, Matthieu,Grach, Guillaume,Abrunhosa, Isabelle,Gulea, Mihaela,Masson, Serge,Vazeux, Michel,Drabowicz, Jozef,Mikolajczyk, Marian
, p. 3406 - 3415 (2007/10/03)
An asymmetric synthesis of benzenesulfinates bearing a phosphonate group at the ortho-position, based on the diastereoselective oxidation of the corresponding sulfenates, has been developed. For this purpose, a number of sulfenates were prepared in high yields by TFFA-promoted condensation of different chiral alcohols with a suitable sulfenyl chloride precursor. Diastereomeric excesses were determined by 31P NMR spectroscopic data with the configuration of the newly created stereogenic centre being assigned through correlation and chemical studies. A practical synthesis of both enantiomers of diisopropyl (2-methylsulfinyl)phenylphosphonate 6 in enantiomeric excess close to 85% is also presented.
