Chiral N-Heterocyclic Carbenes with Restricted Flexibility in Asymmetric Catalysis

A chiral C 2-symmetric diamine was prepared from (S)-3-phenyl-3,4-dihydroisoquinoline by the virtue of asymmetric transformation. Rhodium and iridium complexes of chiral N-heterocyclic carbenes with restricted flexibility derived from 3,3‘-substituted partially reduced biisoquinoline were obtained b...

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Bibliographic Details
Published in:Organometallics 2007-01, Vol.26 (3), p.626-632
Main Authors: Baskakov, Denys, Herrmann, Wolfgang A, Herdtweck, Eberhardt, Hoffmann, Stephan D
Format: Article
Language:English
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Summary:A chiral C 2-symmetric diamine was prepared from (S)-3-phenyl-3,4-dihydroisoquinoline by the virtue of asymmetric transformation. Rhodium and iridium complexes of chiral N-heterocyclic carbenes with restricted flexibility derived from 3,3‘-substituted partially reduced biisoquinoline were obtained by transmetalation from the corresponding silver(I) complexes. Unexpected double-bond formation in the carbene ligand has occurred during a transmetalation step. The structures of these complexes were verified by X-ray diffraction. Metal complexes of these N-heterocyclic carbenes were applied to the asymmetric hydrogenation of methyl 2-acetamidoacrylate. Good enantioselectivities of up to 67% ee were achieved.
ISSN:0276-7333
1520-6041
DOI:10.1021/om0607806