Journal
CATALYSTS
Volume 6, Issue 11, Pages -Publisher
MDPI AG
DOI: 10.3390/catal6110177
Keywords
chiral N-Heterocyclic carbenes; ruthenium catalysts; asymmetric olefin metathesis; enantioselective chromatography; chiro-optical characterization
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Funding
- Ministero dell'Universita e della Ricerca Scientifica e Tecnologica
- Sapienza University of Rome
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In order to design improved chiral ruthenium catalysts for asymmetric olefin metathesis, enantiomeric catalysts incorporating C-1-symmetric N-Heterocyclic carbenes (NHC) ligands with syn-related substituents on the backbone were synthesized starting from meso-1,2-diphenylethylenediamine. The absolute configuration of the enantiomers of the desymmetrized meso diamine was assigned by optical rotation analysis and in silico calculations, and was found to be maintained in their respective ruthenium catalysts by comparison of the relative electronic circular dichroism (ECD) spectra. The catalytic behaviour of the enantiomeric ruthenium complexes was investigated in model asymmetric metathesis transformations and compared to that of analogous complexes bearing C-1-symmetric NHC ligands with an anti backbone. Modest enantioselectivities were registered and different catalyst properties depending on the nature of stereochemical relationship of substituents on the backbone were observed.
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