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Use of a Desymmetrized meso Molecule as a Chiral Ligand: Development of Chiral N‐Heterocyclic Carbene Ligands for Asymmetric Allylic Arylations with Grignard Reagents
Author(s) -
Ando Shin,
Matsunaga Hirofumi,
Ishizuka Tadao
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402089
Subject(s) - chemistry , desymmetrization , carbene , allylic rearrangement , enantioselective synthesis , ligand (biochemistry) , reagent , combinatorial chemistry , catalysis , molecule , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , receptor
The desymmetrization of a meso molecule was used for the development of a chiral N‐ heterocyclic carbene (NHC) ligand. This chiral NHC was then successfully applied to a copper‐catalyzed asymmetric allylic arylation with Grignard reagents. The level of stereocontrol was improved to 89 % ee via derivatization studies. The synthesized copper catalyst was effective at the level of 0.05 mol % loading for gram‐scale reactions.