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Bidentate Hydroxyalkyl NHC Ligands for the Copper‐Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Grignard Reagents
Author(s) -
Magrez Magaly,
Le Guen Yann,
Baslé Olivier,
Crévisy Christophe,
Mauduit Marc
Publication year - 2013
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.201203969
Subject(s) - denticity , tsuji–trost reaction , reagent , allylic rearrangement , chemistry , alkoxy group , enantioselective synthesis , combinatorial chemistry , catalysis , stereochemistry , computer science , organic chemistry , crystal structure , alkyl
Demonstrating their potential : Bidentate alkoxy NHC ligands have been used in the copper‐catalyzed asymmetric allylic alkylation of allyl phosphates with Grignard reagents (see scheme). The method provides access to tertiary and quaternary chiral centers with high regio‐ and enantioselectivity. The system is also applied to the synthesis of chiral E,E ‐dienes, a key structural motif prevalent in natural products.