ChemInform Abstract: Enantioselective Pummerer-Type Rearrangement by Reaction of O- Silylated Ketene Acetal with Enantiopure α-Substituted Sulfoxides.

✍ Scribed by Y. KITA; N. SHIBATA; S. FUKUI; M. BANDO; S. FUJITA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199744092

✦ Synopsis

1997

sulfoxides, sulfones, sulfenes and derivatives sulfoxides, sulfones, sulfenes and derivatives (benzene compounds) Q 0600

44 -092

Enantioselective Pummerer-Type Rearrangement by Reaction of O-Silylated Ketene Acetal with Enantiopure α-Substituted Sulfoxides.

-The sulfoxides (-)-(I) and (-)-(IV) and their enantiomers are found to react with the acetal (II) to give the rearranged α-siloxy sulfides (R)-and (S)-(III), resp., with very high enantioselectivity ( highest reported to date). The reaction of the sulfoxides (V) and (VII) indicates that α-substitution as well as the presence of a pyridyl group are essential for successful and highly stereoselective rearrangement.

-(KITA, Y.;