Enantiopure C1- and C2-symmetric bispidine ligands have been synthesized and screened in the asymmetric copper-catalyzed cyclopropanation of styrene. In order to improve the enantiomeric excesses (ee) of the cyclopropane derivatives, the best performing C1-symmetric diamine ligand was selected for studies on the reaction conditions. The optimized procedure allowed us to obtain up to 91% ee for the cis-cyclopropane derivative and up to 79% ee for the trans one.
Enantioselective copper-catalyzed cyclopropanation of styrene by means of chiral bispidine ligands / G. Lesma, C. Cattenati, T. Pilati, A. Sacchetti, A. Silvani. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 18:5(2007), pp. 659-663. [10.1016/j.tetasy.2007.02.024]
Enantioselective copper-catalyzed cyclopropanation of styrene by means of chiral bispidine ligands
G. LesmaPrimo
;A. SacchettiPenultimo
;A. SilvaniUltimo
2007
Abstract
Enantiopure C1- and C2-symmetric bispidine ligands have been synthesized and screened in the asymmetric copper-catalyzed cyclopropanation of styrene. In order to improve the enantiomeric excesses (ee) of the cyclopropane derivatives, the best performing C1-symmetric diamine ligand was selected for studies on the reaction conditions. The optimized procedure allowed us to obtain up to 91% ee for the cis-cyclopropane derivative and up to 79% ee for the trans one.
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