The reactions of some organocopper reagents with cyclic 2-alkenyl aziridines were examined. The stereoselectivity of the addition reaction of dialkylzinc can be strongly influenced by the use of phosphoramidites as ligands for copper. Chiral copper complexes of 2,2′-binaphthyl-based phosphoramidites were shown to be highly effective catalysts for the regio- (SN2′) and anti-stereoselective addition of dialkylzinc reagents to these compounds according to a kinetic resolution protocol. The corresponding new cyclic allylic amine reaction products were obtained with a good enantioselectivity (83% ee).

Regio- and Enationselective Copper-Catalyzed Addition of Dialkylzinc Reagents to Cyclic 2-Alkenyl Aziridines

PINESCHI, MAURO
2003

Abstract

The reactions of some organocopper reagents with cyclic 2-alkenyl aziridines were examined. The stereoselectivity of the addition reaction of dialkylzinc can be strongly influenced by the use of phosphoramidites as ligands for copper. Chiral copper complexes of 2,2′-binaphthyl-based phosphoramidites were shown to be highly effective catalysts for the regio- (SN2′) and anti-stereoselective addition of dialkylzinc reagents to these compounds according to a kinetic resolution protocol. The corresponding new cyclic allylic amine reaction products were obtained with a good enantioselectivity (83% ee).
Gini, F.; DEL MORO, F.; Macchia, F; Pineschi, Mauro
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/205342
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