Enantioselective organocatalytic Michael additions to acrylic acid derivatives: generation of all-carbon quaternary stereocentres.

Construction of bispirooxindoles containing three quaternary stereocentres in a cascade using a single multifunctional organocatalyst.

Single-step constructions of molecules with multiple quaternary carbon stereocentres are rare. The spirooxindole structural motif is common to a range of bioactive compounds; however, asymmetric synthesis of this motif is complicated due to the presence of multiple chiral centres. The development of organocatalytic cascade reactions has proven to be valuable for the construction of several chir...

Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: access to pipecolic acid derivatives.

The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

A palladium-catalysed enolate alkylation cascade for the formation of adjacent quaternary and tertiary stereocentres

The catalytic enantioselective synthesis of densely functionalised organic molecules containing all-carbon quaternary stereocentres is a challenge to modern chemical methodology research. The catalytically controlled asymmetric alpha-alkylation of ketones represents another difficult task and has been of major interest to our and other research groups in the past. We now report a palladium-cata...

Direct organocatalytic enantioselective mannich reactions of ketimines: an approach to optically active quaternary alpha-amino acid derivatives.

Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Brønsted acid catalyzed self-coupling of enamides.

The enantioselective BINOL-phosphate catalyzed formation of a quaternary carbon center, bearing a N-atom has been achieved through the self-coupling reaction of enamides; the corresponding products have been isolated in up to >99% ee and their application for the synthesis of versatile synthetic building blocks-beta-aminoketones-has been demonstrated.