title: Matching the chirality of monodentate N-heterocyclic carbene ligands: a case study on well-defined palladium complexes for the asymmetric alpha-arylation of amides.
abstract: N-Heterocyclic carbene ligands derived from C(2)-symmetric diamines with naphthyl side chains are introduced as chiral monodentate ligands, and their palladium complexes (NHC)Pd(cin)Cl are prepared. These compounds exist as a mixture of diastereomers, and the palladium complexes can be successfully separated and their absolute stereochemistry assigned. When used in the asymmetric intramolecular alpha-arylation of amides, oxindoles with quaternary carbon centers can be obtained in high yield and selectivity when correctly matching the chirality of the NHC complexes.
authors.affiliation: Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
authors.forename: Xinjun
authors.initials: X
authors.lastname: Luan
authors.forename: Ronaldo
authors.initials: R
authors.lastname: Mariz
authors.forename: Carine
authors.initials: C
authors.lastname: Robert
authors.forename: Michele
authors.initials: M
authors.lastname: Gatti
authors.forename: Sascha
authors.initials: S
authors.lastname: Blumentritt
authors.forename: Anthony
authors.initials: A
authors.lastname: Linden
authors.forename: Reto
authors.initials: R
authors.lastname: Dorta