Asymmetric cyclopropanation of olefins catalysed by Cu(I) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*)

Castano, Brunilde; Guidone, Stefano; Gallo, Emma; Ragaini, Fabio; Casati, Nicola; Macchi, Piero; Sisti, Massimo; Caselli, Alessandro (2013). Asymmetric cyclopropanation of olefins catalysed by Cu(I) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*). Dalton transactions, 42(7), pp. 2451-2462. Cambs, England: Royal Society of Chemistry 10.1039/c2dt32347h

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The synthesis and characterisation of copper(I) complexes of chiral pyridine-containing macrocyclic ligands (Pc-L*) and their use as catalysts in asymmetric cyclopropanation reactions are reported. All ligands and metal complexes were fully characterised, including crystal structures of some species determined by X-ray diffraction on single crystals. This allowed characterising the very different conformations of the macrocycles which could be induced by different substituents or by metal complexation. The strategy adopted for the ligand synthesis is very flexible allowing several structural modifications. A small library of macrocyclic ligands possessing the same donor properties but with either C-1 or C-2 symmetry was synthesized. Cyclopropane products with both aromatic and aliphatic olefins were obtained in good yields and enantiomeric excesses up to 99%.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Macchi, Piero

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

1477-9226

Publisher:

Royal Society of Chemistry

Language:

English

Submitter:

Piero Macchi

Date Deposited:

10 Apr 2014 15:04

Last Modified:

27 Aug 2015 10:21

Publisher DOI:

10.1039/c2dt32347h

BORIS DOI:

10.7892/boris.45663

URI:

https://boris.unibe.ch/id/eprint/45663

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