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Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones

Authors
Mauduit, Marc
Published in Chemistry - A European Journal. 2010, vol. 16, no. 32, p. 9890 - 9904
Abstract The copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclic enones allows the formation of all-carbon chiral quaternary centers. We demonstrate in this article that N-heterocyclic carbenes act as efficient chiral ligands for this transformation. High enantioselectivities (up to 96 % ee) could be obtained for a variety of substrates.
Keywords AsymmetryConjugate additionCopperGrignard reactionN-heterocyclic carbenes
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Other version: http://doi.wiley.com/10.1002/chem.201000471
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KEHRLI, Stefan et al. Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones. In: Chemistry - A European Journal, 2010, vol. 16, n° 32, p. 9890 - 9904. https://archive-ouverte.unige.ch/unige:11963

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Deposited on : 2010-09-30

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