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

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.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-000F-9A0B-E Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0023-C7BC-F

Genre: Journal Article

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Creators:
Figge, A.¹, Author
Altenbach, H. J.¹, Author
Brauer, D. J.¹, Author
Tielmann, P.², Author

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1Berg Univ Gesamthsch Wuppertal, Fachbereich 9, Gaussstr 20, D-; 42097 Wuppertal, Germany;, ou_persistent22
2Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588

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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.

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Language(s): eng - English

Dates: Date issued: 2002-02-28

Publication Status: Issued

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Rev. Type: Peer

Identifiers: eDoc: 20106
DOI: 10.1016/S0957-4166(02)00079-4
ISI: 000175109200007

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Title: Tetrahedron-Asymmetry

Alternative Title : Tetrahedron: Asymmetry

Source Genre: Journal

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Pages: - Volume / Issue: 13 (2) Sequence Number: - Start / End Page: 137 - 144 Identifier: ISSN: 0957-4166