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Chiral C2-Symmetric α-and ω-Diimines with Bulky Substituents at Nitrogen: Synthesis and Catalytic Properties of Some Copper Complexes

  • Published : 2002.05.20
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Abstract

Two new C2-symmetric chiral $\alpha-$ and w-Diimines incorporating bulky ferrocenylethylamine and their copper(I)complexes have been synthesized and characterized by analytical and various spectroscopic techniques. The catalytic activities of these complexes have been tested in the asymmetric cyclopropanation of a series of olefins with some diazoacetates to achieve varying degree of dia- and enantio-selectivities depending on the nature of the ligand, the substrates, and the reagents. Some mechanistic implication has been made with regard to the interactions among all these chemical species.

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References

  1. Van Koten, G.; Vrieze, K. Adv. Organoemet. Chem. 1982, 21,151. https://doi.org/10.1016/S0065-3055(08)60380-9
  2. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev.2000, 100, 2159. https://doi.org/10.1021/cr9902897
  3. Ittel, S. D. L.; Johnson, K.; Brookhart, M.Chem. Rev. 2000, 100, 1169. https://doi.org/10.1021/cr9804644
  4. Britovsek, G. J. P.; Gibson, V. C.;Wass, D. F. Angew. Chem. Int. Ed. 1999, 38, 428. https://doi.org/10.1002/(SICI)1521-3773(19990215)38:4<428::AID-ANIE428>3.0.CO;2-3
  5. Togni, A.;Venanzi, L. M. Angew. Chem. Int. Ed. 1994, 33, 497. https://doi.org/10.1002/anie.199404971
  6. Johnson, L. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc.1996, 118, 267. https://doi.org/10.1021/ja953247i
  7. Mecking, S.; Johnson, L. K.; Wang, L.; Wang,L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888. https://doi.org/10.1021/ja964144i
  8. Johnson,L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117,6414. https://doi.org/10.1021/ja00128a054
  9. Feldman, J.; McLain, S. J.; Parthasarathy, A.; Marshall,W. J.; Calabrese, J. C.; Arthur, S. D. Organometallics 1997, 16,1514. https://doi.org/10.1021/om960968x
  10. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9,2377. https://doi.org/10.1016/S0957-4166(98)00251-1
  11. Kagan, H. B.; Riant, O. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press Inc.: Greenwich, CT, 1997; vol. 2, p 189.
  12. Hayashi, T. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weiheim, Germany, 1995; chapter 2.
  13. Song, J.-H.; Cho, D.-J.; Jeon, S.-J.; Jeong, J.-H.; Kim, T.-J.Inorg. Chem. 1999, 38, 893. https://doi.org/10.1021/ic980433r
  14. Cho, D.-J.; Jeon, S.-J.; Kim, H.S.; Cho, C. S.; Shim, S. C.; Kim, T.-J. Tetrahedron: Asymmetry1999, 10, 3833. https://doi.org/10.1016/S0957-4166(99)00423-1
  15. Kim, T.-J.; Park, D.-K.; Ryu, E.-S.; Jeong, J. H. J. Organomet.Chem. 2002, in press.
  16. Mass, G. Top. Curr. Chem. 1987, 137, 75. https://doi.org/10.1007/3-540-16904-0_15
  17. Doyle, M. P.Asymmetric Cyclopropanation, In Catalytic Asymmetric Synthesis;Ojima, I., Ed.; VCH: Weiheim, 1993; Chapter 3.
  18. Noels, A. F.;Demonceau, A. Catalytic Cyclopropanation, In Applied HomogeneousCatalysis with Organometallic Compounds; Cornil, B.,Hermann, W. A., Eds.: VCH: New York, 1996; chapter 3.
  19. Bedekar, A. V.; Anderson, P. G. Tetrahderon Lett. 1996, 37,4073. https://doi.org/10.1016/0040-4039(96)00736-8
  20. Park, S. B.; Sakata, N.; Nishiyama, H. Chem. Eur. J.1996, 2, 303. https://doi.org/10.1002/chem.19960020311
  21. Uozumi, Y.; Kyota, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1996, 7, 1603. https://doi.org/10.1016/0957-4166(96)00193-0
  22. Gant, T.G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745. https://doi.org/10.1016/0040-4039(95)01924-7
  23. Leutenegger, U.; Umbricht, G.; Fahrni, C.; Matt, P.; Pfaltz, A.Tetrahedron 1992, 48, 2143. https://doi.org/10.1016/S0040-4020(01)88880-3
  24. Evans, D. A.; Woerpel, K. A.;Hinman, M. N.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. https://doi.org/10.1021/ja00002a080
  25. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett.1990, 31, 6005. https://doi.org/10.1016/S0040-4039(00)98014-6
  26. Doyle, M. P.; Bagheri, V.; Wandless, T. T.; Harn, N. K.; Brinker,D. A.; Eagle, C. T.; Loh, K. L. J. Am. Chem. Soc. 1990, 112,1906. https://doi.org/10.1021/ja00161a040
  27. Reigitz, M.; Hocker, J.; Liedhegener, A. Org. Synth. Coll. 1973, V,179.
  28. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta 1988,71, 1553. https://doi.org/10.1002/hlca.19880710621
  29. Kim, S.-G.; Cho, C.-W.; Ahn, K.-H. Tetranhedron: Asymmetry1999, 10, 1903. https://doi.org/10.1016/S0957-4166(99)00190-1
  30. Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. https://doi.org/10.1016/S0040-4039(00)77650-7
  31. Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 10270. https://doi.org/10.1021/ja982488y
  32. Kwong, H.-L.; Lee, W.-S. Tetrahedron: Asymmetry 2000, 11,2299. https://doi.org/10.1016/S0957-4166(00)00182-8
  33. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J.Am. Chem. Soc. 1994, 116, 2223. https://doi.org/10.1021/ja00084a104
  34. Nishiyama, H.; Itoh, Y.;Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc.Jpn. 1995, 68, 1247.
  35. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972,37, 3052. https://doi.org/10.1021/jo00985a002
  36. Marquarding, D.; Gokel, G. W.; Hoffmann, P.; Ugi,I. K. J. Am. Chem. Soc. 1970, 92, 5389. https://doi.org/10.1021/ja00721a017
  37. Bhattacharyya, S. Synth. Commun. 1994, 24, 2713. https://doi.org/10.1080/00397919408010586
  38. Zhuo, J.-C. Magnetic Resonance in Chemistry 1997, 35, 21. https://doi.org/10.1002/(SICI)1097-458X(199701)35:1<21::AID-OMR28>3.0.CO;2-I
  39. Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1982,23, 685. https://doi.org/10.1016/S0040-4039(00)86922-1
  40. Kanemasa, S.; Hamura, S.; Harada, E.; Yamamoto, H.Tetrahedron Lett. 1994, 35, 7985. https://doi.org/10.1016/0040-4039(94)80029-4
  41. Doyle, M. P.; Protopopova,M. N.; Pouller, C. D.; Rogers, D. H. J. Am. Chem. Soc. 1995, 117,7281. https://doi.org/10.1021/ja00132a043
  42. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, A. TetrahedronLett. 1966, 7, 5239. https://doi.org/10.1016/S0040-4039(01)89263-7
  43. Aratani, T. Pure Appl. Chem. 1985, 57,1839. https://doi.org/10.1351/pac198557121839
  44. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911. https://doi.org/10.1021/cr940066a
  45. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Angew. Chem. Int. Ed.Engl. 1986, 25, 1005. https://doi.org/10.1002/anie.198610051
  46. Pfaltz, A. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 533.
  47. Aratani, T.; Yoneyoshi, Y.; Nagase, T.Tetrahedron Lett. 1977, 18, 2599. https://doi.org/10.1016/S0040-4039(01)83830-2
  48. Ichiyanagi, T.; Shimizu, M.;Fujisawa, T. Tetrahedron 1997, 53, 9599. https://doi.org/10.1016/S0040-4020(97)00644-3
  49. Pfaltz, A. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 534.
  50. Doyle, M. P.; McKervey, M. A.; Ye, T. ModernCatalytic Methods for Organic Synthesis with Diazo Compounds;Wiley: New York, 1998.
  51. Calter, M. A. Curr. Org. Chem. 1997,1, 37.
  52. Pfaltz, A. Adv. Catal. Proc. 1995, 1, 61. https://doi.org/10.1016/S1874-5156(06)80006-5
  53. Fritschi, H.; Leutenegger, U.; Siegmann, K.; Pfaltz, A.; Keller, W.;Kratky, C. Helv. Chem. Acta 1988, 71, 1541. https://doi.org/10.1002/hlca.19880710620

Cited by

  1. ChemInform Abstract: Chiral C2-Symmetric α- and ω-Diimines with Bulky Substituents at Nitrogen: Synthesis and Catalytic Properties of Some Copper Complexes. vol.33, pp.38, 2002, https://doi.org/10.1002/chin.200238032