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Novel chiral diimines and diamines derived from sugars in copper-catalysed asymmetric cyclopropanation |
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| Affiliation: | 1. Dipartimento di Scienze Chimiche, Via Marzolo 1, 35131 Padova, Italy;2. Dipartimento di Scienze Chimiche and C.I.R.C.M.S.B., V.le F. Stagno d''Alcontres 31, 98166 Messina, Italy;3. Istituto per lo Studio dei Materiali Nanostrutturati ISMN-CNR c/o Dipartimento di Scienze Chimiche, University of Messina, V.le F. Stagno D''Alcontres, 31-98166 Messina, Italy;4. Dipartimento di Scienze del Farmaco e dei Prodotti per la Salute, V.le Annunziata, 98168 Messina, Italy;5. Department of Chemistry & Biochemistry, Swarthmore College, 500 College Avenue, Swarthmore, PA 19081, USA |
| Abstract: | New chiral diimino and diamino ligands derived from α-d-mannose and α-d-glucose are described. The ligands are obtained by introducing the appropriate nitrogen functions at C(2) and C(3) of the sugar rings. The ability of the new chelates to promote the asymmetric copper(I)-catalysed cyclopropanation of styrene has been investigated. The nature of both the sugars and the chelates is crucial in determining the enantioselectivity of the reaction. |
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