Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 37, Pages 12899-12905Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1032502
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Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft (DFG) through the Center for Functional Nanostructures (CFN) in Karlsruhe
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We present herein the first indications for dimeric structures in cometal-free asymmetric conjugate addition reactions of dialkylzinc reagents with aldehydes. These are revealed by nonlinear effect (NLE) studies. A monomer dimer equilibrium can be assumed which explains the increase of the ee value in the product over time. Also, DOSY NMR spectroscopic measurements indicate the existence of the catalyst as [LZnEt](n) complexes in solution. Additionally, the first X-ray structure of a zinc complex with a [2.2]paracyclophane ligand was determined. The structures of the zinc complexes are supported by DFT calculations of monomeric and dimeric species.
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