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

Figge, A.; Altenbach, H. J.; Brauer, D. J.; Tielmann, P.

doi:10.1016/S0957-4166(02)00079-4

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

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

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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: https://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.