New synthetic routes toward enantiopure nitrogen donor ligands
- Sala, Xavier Departament de Química, Universitat de Girona, Spain
- Rodríguez, Anna M. Departament de Química, Universitat de Girona, Spain
- Rodríguez, Montserrat Departament de Química, Universitat de Girona, Spain
- Romero, Isabel Departament de Química, Universitat de Girona, Spain
- Parella, Teodor Departament de Química, Universitat Autnoma de Barcelona, Spain
- Zelewsky, Alexander von Department of Chemistry, University of Fribourg, Switzerland
- Llobet, Antoni Departament de Química, Universitat de Girona, Spain - Institut Català d'Investigació Química, Tarragona, Spain
- Benet-Buchholz, Jordi Institut Català d'Investigació Química, Tarragona, Spain
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15.11.2006
Published in:
- The Journal of Organic Chemistry. - 2006, vol. 71, no. 25, p. 9283 -9290
English
New polypyridylic chiral ligands, having either C₃ or lower symmetry, have been prepared via a de novo construction of the pyridine nucleus by means of Kröhnke methodology in the key step. The chiral moieties of these ligands originate from the monoterpen chiral pool, namely (-)-α-pinene ((-)-14, (-)-15) and (-)-myrtenal ((-)-9, (-)-10). Extension of the above-mentioned asymmetric synthesis procedure to the preparation of enantiopure derivatives of some commonly used polypyridylic ligands has been achieved through a new aldehyde building block ((-)-16). As an example, the synthesis of a chiral derivative of N,N-bis(2-pyridylmethyl)ethylamine (bpea) ligand, (-)-19, has been performed to illustrate the viability of the method. The coordinative ability of the ligands has been tested through the synthesis and characterization of complexes [Mn((-)-19)Br₂], (-)-20, and [RuCl((-)-10)(bpy)](BF₄), (-)-21. Some preliminary results related to the enantioselective catalytic epoxidation of styrene with the ruthenium complex are also presented.
- Faculty
- Faculté des sciences et de médecine
- Department
- Département de Chimie
- Language
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 8592
- DOI 10.1021/jo0612372
- Persistent URL
- https://folia.unifr.ch/unifr/documents/300647
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