New sugar-derived bifunctional chiral ureas as highly effective organocatalysts in asymmetric aza-Henry reaction. (2nd March 2015)

• Record Type: Journal Article
• Authors: Robak, Jolanta; Kryczka, Bogusław; Świerczyńska, Barbara; Zawisza, Anna; Porwański, Stanisław
• Is Part Of: Carbohydrate research. Volume 404(2015)
• Page Start: 83
• Page End: 86
• Publication Date: 2015-03-02
• Subjects: Aza-Henry -- Saccharides -- Urea -- Organocatalyst; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2014.11.019
• Languages: English
• ISSNs: 0008-6215

Abstract

Graphical abstract: Highlights: The reaction of carbohydrate azides with PPh3 /CO2 and amines is described. Synthesis of new sugar-derive bifunctional chiral urea organocatalysts. Application of new organocatalysts in asymmetric aza-Henry reaction. Enantioselectivity was measured by HPLC. Abstract: A simple synthesis of series of new catalysts derived from chiral bifunctional ureas is described. The aza-Henry reaction of imines with nitromethane was promoted by sugar derived bifunctional organocatalysts to give optically active β-nitroamines. The aza-Henry reaction products were obtained in good yields (35–98%) and ee up to 99%.