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Synthesis of aminophosphines containing a chiral dinaphthoazepine entity and their use in asymmetric catalysis

Synthese von Aminophosphinen mit einer chiralen Dinaphthoazepineinheit und ihre Anwendung in der asymmetrischen Katalyse

  • Organische Chemie Und Biochemie
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Summary

Three azaphospha ligands with a chiral dinaphthoazepine subunit were prepared and used in asymmetric carbon-carbon bond forming reactions. The nickel catalyzedGrignard cross coupling reaction of 1-phenylethyl magnesium chloride and vinyl bromide afforded the product in up to 47% ee. The palladium catalyzed allylic substitution of 1,3-substituted propenylacetates with dimethyl malonate and the coupling of allylacetate with methyl N-(diphenylmethylene)-glycinate resulted in asymmetric inductions of up to 97% ee and 51% ee, respectively.

Zusammenfassung

Drei Azaphospha-Liganden mit einer chiralen Dinaphthoazepineinheit wurden dargestellt und in asymmetrischen Kohlenstoff-Kohlenstoff-Verknüpfungsreaktionen eingesetzt. Bei der nickelkatalysiertenGrignard-Crosskupplung von 1-Phenylethylmagnesiumchlorid mit Vinylbromid erhielt man das Kupplungsprodukt mit bis zu 47% ee. Die palladiumkatalysierte allylische Substitution von 1,3-substituierten Propenylacetaten mit Dimethylmalonat und die Kupplung von Allylacetat mit Methyl-N-(diphenylmethylen)-glycinat zeigten asymmetrische Induktionen von bis zu 97% bzw. 51% ee.

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References

  1. Rosini C, Franzini L, Raffaelli A, Salvadori S (1992) Synthesis 503

  2. Noyori R, Takaya H (1990) Acc Chem Res23: 345

    Google Scholar 

  3. Hotta H, Suzuki T, Miyano S (1990) Chem Lett 143;

  4. Hovorka M, Günterova J, Zavada J (1990) Tetrahedron Lett31: 413;

    Google Scholar 

  5. Smrcina M, Lorenc M, Hanus V, Kocovsky P (1991) Synlett 231;

  6. Gladiali S, Dore A, Fabbri D, De Lucchi O, Manassero M (1994) Tetrahedron: Asymmetry5: 511

    Google Scholar 

  7. Miyano S, Fukushima H, Handa S, Ito H, Hashimoto H (1988) Bull Chem Soc Jpn61: 3249;

    Google Scholar 

  8. Groves JT, Viski P (1990) J Org Chem55: 3628;

    Google Scholar 

  9. Suzuki T, Hotta H, Hattori T, Miyano S (1990) Chem Lett 807;

  10. Hattori T, Shijo M, Kumagai S, Miyano S (1991) Chemistry Express6: 335;

    Google Scholar 

  11. De Lucchi O, Fabbri D, Lucchini V (1991) Synlett 565;

  12. Smrcina M, Lorenc M, Hanus V, Sedmera P, Kocovsky P (1992) J Org Chem57: 1917;

    Google Scholar 

  13. Alcock NW, Brown JM, Pearson M, Woodward S (1992) Tetrahedron: Asymmetry3: 17;

    Google Scholar 

  14. Hayashi T, Uozumi Y (1992) Pure & Appl Chem64: 1911;

    Google Scholar 

  15. Ohta T, Ito M, Inagaki K, Takaya H (1993) Tetrahedron Lett34: 1615;

    Google Scholar 

  16. Uozumi Y, Tanahashi A, Lee S-Y, Hayashi T (1993) J Org Chem58: 1945;

    Google Scholar 

  17. Hattori T, Hotta H, Suzuki T, Miyano S (1993) Bull Chem Soc Jpn66: 613;

    Google Scholar 

  18. Smrcina M, Polakova J, Vyskocil S, Kocovsky P (1993) J Org Chem58: 4534;

    Google Scholar 

  19. Nelson TD, Meyers AI (1994) J Org Chem59: 2655;

    Google Scholar 

  20. Rawal VH, Florjancic AS, Singh SP (1994) Tetrahedron Lett35: 8985;

    Google Scholar 

  21. Stara IG, Stary I, Tichy M, Zavada J, Fiedler P (1994) J Org Chem59: 1326;

    Google Scholar 

  22. Uozumi Y, Suzuki N, Ogiwara A, Hayashi T (1994) Tetrahedron50: 4293

    Google Scholar 

  23. Hayashi T, Konishi M, Fukushima M, Kanehira K, Hioki T, Kumada M (1983) J Org Chem48: 2195;

    Google Scholar 

  24. Sprinz J, Helmchen G (1993) Tetrahedron Lett34: 1769;

    Google Scholar 

  25. Dawson GJ, Frost CG, Williams JMJ, Coote SJ (1993) Tetrahedron Lett34: 3149;

    Google Scholar 

  26. von Matt P, Pfaltz A (1993) Angew Chem105: 614;

    Google Scholar 

  27. Sprinz J, Kiefer M, Helmchen G, Reggelin M, Huttner G, Walter O, Zsolnai L (1994) Tetrahedron Lett35: 1523;

    Google Scholar 

  28. Allen JV, Coote SJ, Dawson GJ, Frost CG, Martin CJ, Williams JMJ (1994) J Chem Soc Perkin Trans 1, 2065;

  29. Dawson GJ, Williams JMJ, Coote SJ (1995) Tetrahedron Lett36: 461;

    Google Scholar 

  30. Eichelmann H, Gais H-J (1995) Tetrahedron: Asymmetry6: 643;

    Google Scholar 

  31. Baldwin IC, Williams JMJ, Beckett RP (1995) Tetrahedron: Asymmetry6: 679;

    Google Scholar 

  32. Dawson GJ, Williams JMJ, Coote SJ (1995) Tetrahedron: Asymmetry6: 2535;

    Google Scholar 

  33. Baldwin IC, Williams JMJ, Beckett RP (1995) Tetrahedron: Asymmetry6: 1515;

    Google Scholar 

  34. Valk J-M, Claridge TDW, Brown JM (1995) Tetrahedron: Asymmetry6: 2597

    Google Scholar 

  35. Wenner W (1951) J Org Chem16: 1475;

    Google Scholar 

  36. Maigrot N, Mazaleyrat J-P, Welvart Z (1985) J Org Chem50: 3916;

    Google Scholar 

  37. Hawkins JM, Fu GC (1986) J Org Chem51: 2820;

    Google Scholar 

  38. Stara IG, Stary I, Zavada J (1992) J Org Chem57: 6966

    Google Scholar 

  39. Hawkins JM, Lewis TA (1992) J Org Chem57: 2114;

    Google Scholar 

  40. Hawkins JM, Lewis TA (1994) J Org Chem59: 649

    Google Scholar 

  41. Wimmer P, Widhalm M (1995) Tetrahedron: Asymmetry6: 657

    Google Scholar 

  42. Kubota H, Koga K (1994) Tetrahedron Lett35: 6689

    Google Scholar 

  43. Maigrot N, Mazaleyrat J-P (1985) Synthesis 317

  44. Hayashi T (1993) Asymmetric Allylic Substitution and Grignard Cross-Coupling. In: Ojima I (ed) Catalytic Asymmetric Synthesis. VCH, Weinheim, pp 325–365

    Google Scholar 

  45. Auburn PA, Mackenzie PB, Bosnich B (1985) J Am Chem Soc107: 2033;

    Google Scholar 

  46. Mackenzie PB, Whelan J, Bosnich B (1985) J Am Chem Soc107: 2046;

    Google Scholar 

  47. Farrar DH, Payne NC (1985) J Am Chem Soc107: 2054

    Google Scholar 

  48. Brown JM, Cooley NA (1988) Chem Rev88: 1031;

    Google Scholar 

  49. Brown JM, Hulmes DI, Guiry PJ (1994) Tetrahedron50: 4493

    Google Scholar 

  50. Hayashi T, Yamamoto A, Ito Y (1986) J Chem Soc (Chem Commun) 1090

  51. Wimmer P (1995) Thesis. University of Vienna

  52. Frost CG, Williams JMJ (1993) Tetrahedron Lett34: 2015;

    Google Scholar 

  53. Dawson GJ, Frost CG, Williams JMJ, Coote SJ (1993) Tetrahedron Lett34: 3149;

    Google Scholar 

  54. Dawson GJ, Frost CG, Martin CJ, Williams JMJ (1993) Tetrahedron Lett34: 7793 and refs. [5b-j]

    Google Scholar 

  55. The program SYBYL (Trypos, version 6.2) was used on a silicon Graphics work station

  56. Hayashi T, Konishi M, Fukushima M, Mise T, Kagotani M, Tajika M, Kumada M (1982) J Am Chem Soc104: 180

    Google Scholar 

  57. Genet JP, Ferroud D, Juge S, Montes JR (1986) Tetrahedron Lett27: 4573;

    Google Scholar 

  58. Genet JP, Juge S, Achi S, Mallart S, Ruiz Montes J, Levif G (1988) Tetrahedron44: 5263;

    Google Scholar 

  59. Burgess K, Ohlmeyer MJ, Whitmire KH (1992) Organometallics11: 3588

    Google Scholar 

  60. Brunner H, Lautenschlager H-J, König WA, Krebber R (1990) Chem Ber123: 847

    Google Scholar 

  61. Cf. Leutenegger U, Umbricht G, Fahrni C, von Matt P, Pfaltz A (1992) Tetrahedron48: 2143

    Google Scholar 

  62. Sennhenn P, Gabler B, Helmchen G (1994) Tetrahedron Lett35: 8595

    Google Scholar 

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Austria

    P. Wimmer & M. Widhalm

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  1. P. Wimmer
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  2. M. Widhalm
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Wimmer, P., Widhalm, M. Synthesis of aminophosphines containing a chiral dinaphthoazepine entity and their use in asymmetric catalysis. Monatsh Chem 127, 669–681 (1996). https://doi.org/10.1007/BF00817258

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  • DOI: https://doi.org/10.1007/BF00817258

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