CARBOHYDRATE PHOSPHINITES AS CHIRAL LIGANDS FOR ASYMMETRIC SYNTHESES CATALYZED BY COMPLEXES .10. IMPORTANCE OF ALL-EQUATORIAL ARRANGEMENT IN VICINAL BISPHOSPHINITE HEXAPYRANOSIDE LIGANDS FOR RHODIUM-CATALYZED ASYMMETRIC HYDROGENATION

Authors
SELKE R SCHWARZE M BAUDISCH H GRASSERT I MICHALIK M OEHME G STOLL N COSTISELLA B
Citation
R. Selke et al., CARBOHYDRATE PHOSPHINITES AS CHIRAL LIGANDS FOR ASYMMETRIC SYNTHESES CATALYZED BY COMPLEXES .10. IMPORTANCE OF ALL-EQUATORIAL ARRANGEMENT IN VICINAL BISPHOSPHINITE HEXAPYRANOSIDE LIGANDS FOR RHODIUM-CATALYZED ASYMMETRIC HYDROGENATION, Journal of molecular catalysis, 84(3), 1993, pp. 223-237
Citations number
60
Categorie Soggetti
Chemistry Physical
Journal title
Journal of molecular catalysis → ACNP
ISSN journal
03045102
Volume
84
Issue
3
Year of publication
1993
Pages
223 - 237
Database
ISI
SICI code
0304-5102(1993)84:3<223:CPACLF>2.0.ZU;2-Z
Abstract
The application of some newly prepared aryl 3-bis(O-diphenylphosphino) -beta-D-glucopyranosides 4b-g in form of their rhodium(I) chelates as catalysts in asymmetric hydrogenation of dehydroamino acid derivatives shows similar high enantioselectivities to the parent ligand Ph-beta- glup 4a whose chelate has found industrial application for production of L-dopa. The importance of all-equatorial arrangement of the pyranos ide substituents for enantioselectivities of more than 90% ee is demon strated by comparison with analogous structures carrying axial groups and a rule could be set up. A spectroscopic investigation of some impo rtant representatives is added.