Chiral Phosphinopyrrolyl-Oxazolines: A New Class of Easily Prepared, Modular P,N-Ligands

Advanced Synthesis and Catalysis

Volumn 343, Issue 5, 2001, Pages 450-454

  Cozzi, Pier Giorgio ^a   Zimmermann, Nicole ^b   Hilgraf, Robert ^b   Schaffner, Silvia ^b   Pfaltz, Andreas ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Allylation; Asymmetric catalysis; Hydrogenation; Iridium; Palladium; Phosphinooxazolines

Indexed keywords

EID: 0001596428     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200107)343:5<450::AID-ADSC450>3.0.CO;2-7     Document Type: Article

References (33)

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16. N-Phosphinoindolyloxazolines were also prepared, using a different route starting from indole-2-carboxylic acid (P. G. Cozzi, unpublished results).
17. Analogous phosphines derived from 4 were found to be unstable and could not be isolated in pure form.
18. Ligand 8 was obtained as an oil.
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24. A. Lightfoot, P. Schnider, A. Pfaltz, Angew. Chem. 1998, 110, 3047-3050; Angew. Chem. Int Ed. Engl. 1998, 37, 2897-2899.
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27. -3. Geometric restraints were applied to parts of the TFPB moieties and the solvent molecules, hydrogen atoms were calculated and refined as riding atoms. Data collection was performed with a KappaCCD spectrometer. Programs used: structure solution SIR92 (A. Altomare, G. Cascarano, C. Giaccovazzo, A. Gualgliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435), structure refinement CRYSTALS (D. J. Watkin, 'Crystals, Issue 9', Chemical Crystallography Laboratory, Oxford, 1990), weighting scheme: Chebychev polynominal (J. R. Carruthers, D. J. Watkin, Acta Crystallogr., Sect. A 1979, 35, 698) , graphics SNOOPI (K. Davies, P. Braid, B. Foxman, H. Powell, Oxford University, 1989). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Date Centre as deposition No. CCDC-163734. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223) 336 033; e-mail: deposit@ccdc.cam.ac.uk].
28. -3. Geometric restraints were applied to parts of the TFPB moieties and the solvent molecules, hydrogen atoms were calculated and refined as riding atoms. Data collection was performed with a KappaCCD spectrometer. Programs used: structure solution SIR92 (A. Altomare, G. Cascarano, C. Giaccovazzo, A. Gualgliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435), structure refinement CRYSTALS (D. J. Watkin, 'Crystals, Issue 9', Chemical Crystallography Laboratory, Oxford, 1990), weighting scheme: Chebychev polynominal (J. R. Carruthers, D. J. Watkin, Acta Crystallogr., Sect. A 1979, 35, 698) , graphics SNOOPI (K. Davies, P. Braid, B. Foxman, H. Powell, Oxford University, 1989). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Date Centre as deposition No. CCDC-163734. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223) 336 033; e-mail: deposit@ccdc.cam.ac.uk].
29. -3. Geometric restraints were applied to parts of the TFPB moieties and the solvent molecules, hydrogen atoms were calculated and refined as riding atoms. Data collection was performed with a KappaCCD spectrometer. Programs used: structure solution SIR92 (A. Altomare, G. Cascarano, C. Giaccovazzo, A. Gualgliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435), structure refinement CRYSTALS (D. J. Watkin, 'Crystals, Issue 9', Chemical Crystallography Laboratory, Oxford, 1990), weighting scheme: Chebychev polynominal (J. R. Carruthers, D. J. Watkin, Acta Crystallogr., Sect. A 1979, 35, 698) , graphics SNOOPI (K. Davies, P. Braid, B. Foxman, H. Powell, Oxford University, 1989). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Date Centre as deposition No. CCDC-163734. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223) 336 033; e-mail: deposit@ccdc.cam.ac.uk].
30. -3. Geometric restraints were applied to parts of the TFPB moieties and the solvent molecules, hydrogen atoms were calculated and refined as riding atoms. Data collection was performed with a KappaCCD spectrometer. Programs used: structure solution SIR92 (A. Altomare, G. Cascarano, C. Giaccovazzo, A. Gualgliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435), structure refinement CRYSTALS (D. J. Watkin, 'Crystals, Issue 9', Chemical Crystallography Laboratory, Oxford, 1990), weighting scheme: Chebychev polynominal (J. R. Carruthers, D. J. Watkin, Acta Crystallogr., Sect. A 1979, 35, 698) , graphics SNOOPI (K. Davies, P. Braid, B. Foxman, H. Powell, Oxford University, 1989). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Date Centre as deposition No. CCDC-163734. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223) 336 033; e-mail: deposit@ccdc.cam.ac.uk].
31. P. Schnider, G. Koch, R. Prétôt, G. Wang, F. M. Bohnen, C. Krüger, A. Pfaltz, Chem. Eur. J. 1997, 3, 887-892.
32. For Ti- and Zr-catalyzed enantioseleclive hydrogenation of unfunctionalized olefins, see: R. D. Broene, S. L. Buchwald, J. Am. Chem. Soc. 1993, 115, 12569-12570; M. V. Troutman, D. H. Appella, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4916-4917.
33. For Ti- and Zr-catalyzed enantioseleclive hydrogenation of unfunctionalized olefins, see: R. D. Broene, S. L. Buchwald, J. Am. Chem. Soc. 1993, 115, 12569-12570; M. V. Troutman, D. H. Appella, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 4916-4917.