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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Veröffentlicht in:	Chemistry : a European journal 2015-01, Vol.21 (3), p.993-7
Hauptverfasser:	Jahier-Diallo, Claire, Morin, Marie S T, Queval, Pierre, Rouen, Mathieu, Artur, Isabelle, Querard, Pierre, Toupet, Loic, Crévisy, Christophe, Baslé, Olivier, Mauduit, Marc
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Sprache:	eng
Schlagworte:	Chemical Sciences
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container_title	Chemistry : a European journal
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creator	Jahier-Diallo, Claire Morin, Marie S T Queval, Pierre Rouen, Mathieu Artur, Isabelle Querard, Pierre Toupet, Loic Crévisy, Christophe Baslé, Olivier Mauduit, Marc
description	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.).
doi_str_mv	10.1002/chem.201405765
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title	Multicomponent Synthesis of Chiral Bidentate Unsymmetrical Unsaturated N-Heterocyclic Carbenes: Copper-Catalyzed Asymmetric C Bond Formation
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