Regio- and enantioselective copper-catalyzed addition of dialkylzinc reagents to cyclic 2-alkenyl aziridines |
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Authors: | Francesca GiniFederica Del Moro Franco MacchiaMauro Pineschi |
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Affiliation: | Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy |
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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). |
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