de.mpg.escidoc.pubman.appbase.FacesBean
English
 
Help Guide Disclaimer Contact us Login
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen- 1-yl)-1-isopropyl-1H-benzoimidazole; a new atropisomeric P,N- chelating ligand for asymmetric catalysis

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons59049

Tielmann,  P.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Locator
There are no locators available
Fulltext (public)
There are no public fulltexts available
Supplementary Material (public)
There is no public supplementary material available
Citation

Figge, A., Altenbach, H. J., Brauer, D. J., & Tielmann, P. (2002). Synthesis and resolution of 2-(2-diphenylphosphinyl-naphthalen- 1-yl)-1-isopropyl-1H-benzoimidazole; a new atropisomeric P,N- chelating ligand for asymmetric catalysis. Tetrahedron-Asymmetry, 13(2), 137-144. doi:10.1016/S0957-4166(02)00079-4.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-9A0B-E
Abstract
A multistep synthesis resulting in a good yield of the title compound 13 (BIMNAP) has been developed based on N,N-acetal- formation and oxidation with MnO2. The product 11 is converted into the corresponding trifluoromethane sulfonate 12 by treatment with (CF3SO2)(2)O followed by a nickel-catalysed coupling-reaction with HPPh2. Resolution of the phosphanamine 13 was carried out via fractional crystallisation of the diastereomeric hexafluorophosphate salts of the Pd-complex 15, formed from reaction of 13 with (+)-di-mu-chlorobis{2-[1- (dimethylamino)ethyl]phenyl-C,N}dipalladium (S)-14. The absolute configurations of the two diastereomers were determined by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.