Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 28, Pages 5441-5446Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100488
Keywords
Asymmetric catalysis; Michael addition; Nitroalkenes; N ligands; Noncovalent interactions
Categories
Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft (DFG) [CZ 183/1-1]
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A chiral C-2-symmetric 1,2-diamine based on a 1,1'-bi(tetrahydroisoquinoline) scaffold was found to be an efficient ligand for the enantioselective Ni-II-catalysed Michael addition of malonic esters to conjugated nitroalkenes. The reactions proceed with 92-99% yield and 91-99% enantioselectivity even at elevated temperatures. The solid-state structure of the catalyst precursor revealed intramolecular pi-pi stacking as well as supramolecular halogen center dot center dot center dot halogen bonding interactions.
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