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Catalysts 2016, 6(11), 177; doi:10.3390/catal6110177

Enantiopure C1-symmetric N-Heterocyclic Carbene Ligands from Desymmetrized meso-1,2-Diphenylethylenediamine: Application in Ruthenium-Catalyzed Olefin Metathesis

1
Dipartimento di Chimica e Biologia “Adolfo Zambelli”, Università di Salerno, Via Giovanni Paolo II 132, I-84084 Fisciano, Salerno, Italy
2
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Piazzale A. Moro 5, 00185 Roma, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Federico Cisnetti
Received: 14 October 2016 / Revised: 8 November 2016 / Accepted: 9 November 2016 / Published: 14 November 2016
(This article belongs to the Special Issue Tailor-Made NHC Ligands)
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Abstract

In order to design improved chiral ruthenium catalysts for asymmetric olefin metathesis, enantiomeric catalysts incorporating C1-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 C1-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. View Full-Text
Keywords: chiral N-Heterocyclic carbenes; ruthenium catalysts; asymmetric olefin metathesis; enantioselective chromatography; chiro-optical characterization chiral N-Heterocyclic carbenes; ruthenium catalysts; asymmetric olefin metathesis; enantioselective chromatography; chiro-optical characterization
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MDPI and ACS Style

Paradiso, V.; Menta, S.; Pierini, M.; Della Sala, G.; Ciogli, A.; Grisi, F. Enantiopure C1-symmetric N-Heterocyclic Carbene Ligands from Desymmetrized meso-1,2-Diphenylethylenediamine: Application in Ruthenium-Catalyzed Olefin Metathesis. Catalysts 2016, 6, 177.

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