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

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 conjuga...

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Published inChemistry : a European journal Vol. 21; no. 3; pp. 993 - 7
Main Authors Jahier-Diallo, Claire, Morin, Marie S T, Queval, Pierre, Rouen, Mathieu, Artur, Isabelle, Querard, Pierre, Toupet, Loic, Crévisy, Christophe, Baslé, Olivier, Mauduit, Marc
Format Journal Article
LanguageEnglish
Published Wiley-VCH Verlag 12.01.2015
Subjects
Chemical Sciences
quaternary carbon atoms
bifunctional ligands
multicomponent synthesis
asymmetric catalysis
chiral NHCs
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Summary: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.).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201405765