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Multicomponent Synthesis of Chiral Bidentate Unsymmetrical Unsaturated N ‐Heterocyclic Carbenes: Copper‐Catalyzed Asymmetric CC Bond Formation
Author(s) -
JahierDiallo Claire,
Morin Marie S. T.,
Queval Pierre,
Rouen Mathieu,
Artur Isabelle,
Querard Pierre,
Toupet Loic,
Crévisy Christophe,
Baslé Olivier,
Mauduit Marc
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405765
Subject(s) - stereocenter , chemistry , carbene , tsuji–trost reaction , denticity , catalysis , allylic rearrangement , enantioselective synthesis , copper , alkylation , quaternary carbon , medicinal chemistry , organic chemistry , stereochemistry , combinatorial chemistry , metal
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.).