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Benaglia M, Benincori T, Mussini P, et al. Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone. J Org Chem. 2005;70(19):7488-95doi: 10.1021/jo050267m.
Benaglia, M., Benincori, T., Mussini, P., Pilati, T., Rizzo, S., & Sannicolò, F. (2005). Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone. The Journal of organic chemistry, 70(19), 7488-95. https://doi.org/10.1021/jo050267m
Benaglia, Maurizio, et al. "Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone." The Journal of organic chemistry vol. 70,19 (2005): 7488-95. doi: https://doi.org/10.1021/jo050267m
Benaglia M, Benincori T, Mussini P, Pilati T, Rizzo S, Sannicolò F. Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone. J Org Chem. 2005 Sep 16;70(19):7488-95. doi: 10.1021/jo050267m. PMID: 16149775.
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J Org Chem. 2005 Sep 16;70(19):7488-95. doi: 10.1021/jo050267m.

Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone.

The Journal of organic chemistry

Maurizio Benaglia, Tiziana Benincori, Patrizia Mussini, Tullio Pilati, Simona Rizzo, Franco Sannicolò

Affiliations

  1. Dipartimento di Chimica Organica e Industriale dell'Università, via Golgi 19-20133 Milano, Italy. [email protected]

PMID: 16149775 DOI: 10.1021/jo050267m

Abstract

[structure: see text] The role played by the electronic properties and the steric features of bis(oxazoline) ligands in the Cu(I)-catalyzed cyclopropanation of styrene effected with ethyl diazoacetate was investigated. Two pairs of new bis(oxazolines) displaying flexible and atropisomeric 3,3'-bithiophene backbones were synthesized and structurally and electronically characterized. For the first time, the electrochemical oxidative potential was used as a reliable index of the electronic density on the nitrogen atom of the chelating groups of new and, for comparative purposes, of already known bis(oxazolines). The Cu(I) complexes of the new ligands were prepared, and their enantioselection ability and catalytic efficiency were tested. This investigation suggests that steric factors and catalyst geometrical features are clearly more important than any consideration of the electronic properties of the chiral ligands.

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