Diastereoselective synthesis of quaternary substituted thioindolines from sulfur ylide intermediates

✍ Scribed by Alexei V Novikov; Amir Sabahi; Abijah M Nyong; Jon D Rainier

• Book ID: 104359688
• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 267 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00077-6

✦ Synopsis

We have examined the coupling reactions of 2-thioindoles with vinyl diazoacetates in the presence of Rh(II) catalysts. While attempted enantio-and/or diastereoselective couplings using chiral catalysts and/or chiral auxiliaries on the vinyl diazoacetate have been largely unsuccessful, substrates having resident chirality on fused thiopyrans gave thioindolines with moderate to high diastereoselectivities.