Generalized anomeric effect in gem-diamines: stereoselective synthesis of alpha-N-linked disaccharide mimics
Elena M Sánchez-Fernández1, Rocío Rísquez-Cuadro, Matilde Aguilar-Moncayo
1Instituto de Investigaciones Químicas, CSIC and Universidad de Sevilla, Isla de la Cartuja, E-41092 Sevilla, Spain.
Abstract:
The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable alpha-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase.
Related Concept Videos
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis


