A variety of new chiral phosphoramidites was synthesised and tested in the copper-catalysed enantioselective conjugate addition of diethylzinc to cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.’s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic and acyclic enones.

Enantioselective Catalytic Conjugate Addition of Dialkylzinc Reagents using Copper-Phosphoramidite Complexes; Ligand Variation and Non-linear Effects

MANDOLI, ALESSANDRO;
2000

Abstract

A variety of new chiral phosphoramidites was synthesised and tested in the copper-catalysed enantioselective conjugate addition of diethylzinc to cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.’s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic and acyclic enones.
L. A., Arnold; R., Imbos; Mandoli, Alessandro; A. H. M., DE VRIES; R., Naasz; B. L., Feringa
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/166940
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