Asymmetric oxidation of sulfides using (salen)manganese(III) complex as a catalyst

✍ Scribed by Kenji Noda; Naoki Hosoya; Koichi Yanai; Ryo Irie; Tsutomu Katsuki

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 313 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73187-x

✦ Synopsis

Asymmetric oxidation of sulfides is one of current topics and many useful methodologies for this purpose have been mported to date.13) Some of these methodologies are well known to be also useful for the epexidation of olefins. However, differing from epoxidation, there is no good methodology for catalytic asymmetric oxidation of sulfides, though some stoichiometric reactions show high enanticselectivity &90% ee).lJb) Recently we found that optically active (salen)manganese(III) complexes having asymmetric carbons at C8, Cg, Cl", and C2" were efficient catalysts for asymmetric epoxidation of simple olefins (Scheme 1)P)

To extend the scope of this-type of salen catalyst and to develop an efficient methodology fcr catalytic asymmetric oxidation of sulfides, we examined oxidation of sulfides using these salen complexes as catalysts.~ lralb.PhIO la: 78%,%% ee lb : 86%. 75% ee