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Multicomponent Synthesis of Chiral Bidentate Unsymmetrical Unsaturated N-Heterocyclic Carbenes: Copper-Catalyzed Asymmetric C Bond Formation

Abstract : A multicomponent strategy was applied to the synthesis of chiral bidentate unsaturated hydroxyalkyl- and carboxyalkyl-N-heterocyclic carbene (NHC) precursors. The newly developed low-cost chiral ligands derived from amino alcohols and amino acids were evaluated in copper-catalyzed asymmetric conjugated addition and asymmetric allylic alkylation, which afforded the desired tertiary and quaternary carbon stereocenters with excellent regio- and enantioselectivities (up to 99:1 e.r.).
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01114852
Contributor : Laurent Jonchère <>
Submitted on : Tuesday, February 10, 2015 - 10:08:06 AM
Last modification on : Thursday, March 5, 2020 - 2:05:34 PM

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Claire Jahier-Diallo, Marie S T Morin, Pierre Queval, Mathieu Rouen, Isabelle Artur, et al.. Multicomponent Synthesis of Chiral Bidentate Unsymmetrical Unsaturated N-Heterocyclic Carbenes: Copper-Catalyzed Asymmetric C Bond Formation. Chemistry - A European Journal, Wiley-VCH Verlag, 2015, 21 (3), pp.993-7. ⟨10.1002/chem.201405765⟩. ⟨hal-01114852⟩

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