Stereoselective cycloaddition of 1-glucosyl-1,3-butadienes with tert-butyl 2H-a...

• Author(s): Alves, M. José ; Almeida, I. G. ; Fortes, A. Gil ; Freitas, A. P.
• Date: 2003
• Persistent ID: http://hdl.handle.net/1822/1843
• Origin: RepositóriUM - Universidade do Minho
• Subject(s): Cycloaddition; 1,3-butadienes; 2H-azirines; Glyoxylates; Imines
• Document Type: Article
• Language: English

Description

Glucosyl dienes 1 have been reacted with the achiral 2H-azirine 4 and with glyoxylates, forming fused structures of type 5 and disaccharide-like compounds 7 with good to excellent selectivity. Glucosyl dienes 1 participated as dienophiles in reactions with Schiff bases derived from anilines forming isoquinolines 10 and 11. The diastereoselectivity of this reaction is poor.