Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 2, Pages 178-187Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701452
Keywords
Asymmetric catalysis; Nitroaldol reaction; Diamide ligands; Copper; DFT calculations
Categories
Funding
- Centre National de la Recherche Scientifique (CNRS)
- Universite de Montpellier
- Universite de Lorraine
- CINES/CEA CCRT/IDRIS [A0010807449]
Ask authors/readers for more resources
Chiral tetra- and bidentate ligands derived from the (R)-1,2-diaminobicyclo[2.2.2]octane scaffold were synthesized, and the influence of the N,N-substituents of the ligand on the catalytic activity of their corresponding copper(II) complexes toward the nitroaldol reaction was investigated. Among them, the complex generated in situ by the interaction of the (R)-N,N-bis(1-naphthylmethyl)-1,2-diaminobicyclo[2.2.2]octane ligand with Cu(OAc)(2) proved to be the most effective for the asymmetric Henry reaction of nitromethane with various aldehydes to provide -nitro alcohols in moderate to good yields and good enantioselectivity (up to 86%). In an attempt to rationalize the factors that control enantiodifferentiation, the most stable geometries of this C-1-symmetric bicyclic copper ligand complex and the plausible transition structures of the nitroaldol reaction were investigated by DFT calculations.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available