Journal
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Volume -, Issue 13, Pages 1989-1999Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejic.200801243
Keywords
Asymmetric catalysis; Diaminocarbene; Carbene ligands; Ligand design; Conjugate addition; Atropisomerism
Categories
Funding
- Centre National de la Recherche Scientifique (CNRS)
- Region Bretagne
- Ministere de la Recherche et de la Technologic
- Agence Nationale de la Recherche (ANR) (CP2D/RDR2 program)
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The design and the synthesis of a set of new chiral hydroxyalkyl- and hydroxyaryl-chelating diaminocarbene ligands is reported. Comparative catalytic studies show the importance of the scaffold design around the NHC unit to obtain a high enantiocontrol in Cu-catalyzed asymmetric conjugate addition (ACA). Whereas low selectivities are observed when the stereogenic centre is placed within the N-heterocyclic ring, an interesting match effect can be observed when central chirality is located within both of the two side chains, which enables up to 92 % ee in the catalysis reaction. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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