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

Claire Jahier-Diallo 1 Marie S T Morin 1 Pierre Queval 1 Mathieu Rouen 1 Isabelle Artur 1 Pierre Querard 1 Loic Toupet 2 Christophe Crévisy 1 Olivier Baslé 1 Marc Mauduit 1
1 ISCR - Institut des Sciences Chimiques de Rennes
2 IPR - Institut de Physique de Rennes
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.).
Keywords : chiral NHCs bifunctional ligands asymmetric catalysis multicomponent synthesis quaternary carbon atoms
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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 : Tuesday, April 20, 2021 - 5:52:02 PM

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UNIV-RENNES1 | ISCR | IPR | CNRS | ISCR-OMC | INC-CNRS | UR1-UFR-SPM | OSUR | UNIV-RENNES | INSA-GROUPE | IPR-ML | INSA-RENNES

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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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