Asymmetric oxidation of sulfides with H2O2 catalyzed by titanium complexes with aminoalcohol derived Schiff bases

✍ Scribed by Konstantin P. Bryliakov; Evgenii P. Talsi

• Publisher: Elsevier Science
• Year: 2007
• Tongue: English
• Weight: 551 KB
• Volume: 264
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/j.molcata.2006.09.038

✦ Synopsis

Sulfoxidation catalysts generated in situ from titanium(IV) isopropoxide and enantiopure Schiff bases promote the enantioselective oxidation of alkyl aryl sulfides to the corresponding sulfoxides at low catalyst loadings (<1 mol%), 30% aqueous hydrogen peroxide being the terminal oxidant. Upon screening of several ligands derived from ␤-aminoalcohols and salicylaldehydes, a catalyst affording sulfoxides with over 90% chemoselectivity and up to 60% ee was found, and the kinetics of the catalytic reaction was analyzed by 1 H NMR.