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Function of an N-Heterocyclic Carbene Ligand Based on Concept of Chiral Mimetic

2006; Pharmaceutical Society of Japan; Volume: 54; Issue: 11 Linguagem: Inglês

10.1248/cpb.54.1576

1347-5223

Takafumi Arao, Kei Sato, Kazuhiro Kondo, Toyohiko Aoyama,

Synthetic Organic Chemistry Methods

Function of a new N-heterocyclic carbene ligand based on the concept of a chiral mimetic is described. With (4R,5R)-4,5-diphenyl-1,3-dialkyl-4,5-dihydro-3H-imidazol-1-ium tetrafluoroborates as N-heterocyclic carbene precursors, Rh-catalyzed enantioselective arylation (up to 27% ee) of aromatic aldehydes with arylboronic acids and Pd-catalyzed enantioselective intramolecular α-arylation (up to 66% ee) of N-(2-bromoaryl)-N-alkyl-2-arylpropanamides are investigated.