Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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1,2-Ferrocenedilazaphosphinines 3:A New Class fo Planar Chiral Ligands for Cu-Catalyzed Cyclopropanation

  • Paek, Seung-Hwan (Department of Industrial Chemistry, Kyungpook National University) ;
  • Co, Thanh Thien (Department of Industrial Chemistry, Kyungpook National University) ;
  • Lee, Dong-Ho (Department of Polymer Science, Kyungpook National University) ;
  • Park, Yu-Chul (Department of Chemistry, Kyungpook National University) ;
  • Kim, Tae-Jeong (Department of Industrial Chemistry, Kyungpook National University)
  • Published : 2002.12.20
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Abstract

The synthesis and catalytic application of a new class of a new class of planar chiral ferrocenes, 1,2-ferrocenediylazaphosphinines (1 and 2) are described. They are powerful ligands for the copper(I)-catalyzed asymmetric cyclopropanation of a range of alkenes with diazo esters to exhibit an exceptionally high degree of diastereoselectivity(~100% de) in favor of trans isomers, regardless the structure of the olefins and the diazo compounds. Comparative studies between 1 and 2 reveal that the former works better in terms of diastereocontrol. In contrast, however, enantioselectivity is low with both 1 and 2 as a whole although, in certain cases with a proper combination of the olefin and the diazo ester, high optical yields (up to 100% ee) can be achieved. Other reaction parameters such as the reaction temperature and the structure of the ligand do exhibit some influence, although infinitestimal, on both chemical and optical yields.

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References

  1. Syn Lett 2002 (accepted for publication).
  2. Doyle, M. P. Asymmetric Addition and Insertion Reactions of Catalytically-Generated Metal Carbenes, in Catalytic Asymmetric Synthesis; Ojima I., Ed.; Wiley-VCH: New York, 2000; chapter 5.
  3. Pfaltz, A. Cyclopropanation and C-H Insertion with Cu, in Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999; chapter 16.1.
  4. Lydon, K. M.; McKervey, M. A. Cyclopropanation and C-H Insertion with Rh, in Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999; chapter 16.2.
  5. Charette, A. B.; Lebel, H. Cyclopropanation and C-H Insertion with Metals Other than Cu and Rh, in Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999; chapter 16.3.
  6. Noels, A. F.; Demonceau, A. Catalytic Cyclopropanation, in Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herman W. A., Eds.; VCH: New York, 1996; chapter 3.
  7. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 5239.
  8. Doyle, M. P. Chem. Rev. 1986, 19, 348 https://doi.org/10.1021/ar00131a004
  9. Doyle, M. P. Acc. Chem. Res. 1986, 19, 348. https://doi.org/10.1021/ar00131a004
  10. Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1975, 1707.
  11. Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1977, 2599.
  12. Dauben, W. G.; Hendricks, R. T.; Luzzio, M. J.; Ng, H. P. Tetrahedron Lett. 1990, 31, 6969. https://doi.org/10.1016/S0040-4039(00)97218-6
  13. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Angew. Chem., Int. Ed. 1986, 25, 1005. https://doi.org/10.1002/anie.198610051
  14. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1553. https://doi.org/10.1002/hlca.19880710621
  15. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. https://doi.org/10.1021/ar00030a007
  16. Rowental, R. E.; Abiko, A.; Masamine, S. Tetrahedron Lett. 1990, 31, 6005. https://doi.org/10.1016/S0040-4039(00)98014-6
  17. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. https://doi.org/10.1002/hlca.19910740123
  18. Evans, D. A.; Woerpal, K. A.; Hinman, M. M. J. Am. Chem. Soc. 1991, 113, 726. https://doi.org/10.1021/ja00002a080
  19. Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745. https://doi.org/10.1016/0040-4039(95)01924-7
  20. Uozumi, Y.; Kyota, H.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1996, 7, 1603. https://doi.org/10.1016/0957-4166(96)00193-0
  21. Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1996, 37, 4073. https://doi.org/10.1016/0040-4039(96)00736-8
  22. Kim, S.-G.; Cho, C.-W.; Ahn, K.-H. Tetrahedron: Asymmetry 1997, 8, 1023. https://doi.org/10.1016/S0957-4166(97)00097-9
  23. Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599. https://doi.org/10.1016/S0040-4020(97)00644-3
  24. Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007. https://doi.org/10.1021/jo9807417
  25. Ito, K.; Tabuchi, S.; Katsuki, T. Synlett 1992, 575.
  26. Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. https://doi.org/10.1016/S0040-4039(00)77650-7
  27. Ito, K.; Katsuki, T. Synlett 1993, 638.
  28. Brunner, H.; Singh, U. P.; Boeck, T.; Altman, S.; Scheck, T.; Wrackmeyer, B. J. Organomet. Chem. 1993, 443, C16. https://doi.org/10.1016/0022-328X(93)80027-9
  29. Perez, P. J.; Brookhart, M.; Templeton, J. L. Organometallics 1993, 12, 261. https://doi.org/10.1021/om00026a007
  30. Diaz-Requejo, M. M.; Perez, P. J.; Brookhart, M.; Templeton, J. L. Organometallics 1997, 16, 4399. https://doi.org/10.1021/om970382q
  31. Diaz-Requejo, M. M.; Nicasio, M. C.; Perez, P. J. Organometallics 1998, 17, 3051. https://doi.org/10.1021/om980061u
  32. Callot, H. J.; Metz, F.; Piechoki, C. Tetrahedron 1982, 38, 2365. https://doi.org/10.1016/0040-4020(82)87014-2
  33. O'Malley, S.; Kodadek, T. J. Am. Chem. Soc. 1989, 111, 9116. https://doi.org/10.1021/ja00207a027
  34. O'Malley, S.; Kodadek, T. Tetrahedron Lett. 1991, 32, 2445. https://doi.org/10.1016/S0040-4039(00)74349-8
  35. O'Malley, S.; Kodadek, T. Organometallics 1992, 11, 2299. https://doi.org/10.1021/om00042a052
  36. Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326. https://doi.org/10.1021/ja00065a067
  37. Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889. https://doi.org/10.1021/ja00126a044
  38. Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 10270. https://doi.org/10.1021/ja982488y
  39. Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377.
  40. Hwang, G.-H.; Ryu, E.-S.; Park, D.-K.; Shim, S. C.; Cho, C. S.; Kim, T.-J.; Jeong, J. H.; Cheong, M. Organometallics 2001, 20, 5784. https://doi.org/10.1021/om010603z
  41. Cho, D.-J.; Jeon, S.-J.; Kim, H.-S.; Kim, T.-J. Synlett 1998, 617.
  42. Song, J.-H.; Cho, D.-J.; Jeon, S.-J.; Kim, Y.-H.; Kim, T.-J.; Jeong, J.-H. Inorg. Chem. 1999, 38, 893. https://doi.org/10.1021/ic980433r
  43. Cho, D.-J.; Jeon, S.-J.; Kim, H.-S.; Cho, C. S.; Shim, S. C.; Kim, T.-J.; Tetrahedron: Asymmetry 1999, 10, 3833. https://doi.org/10.1016/S0957-4166(99)00423-1
  44. Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503. https://doi.org/10.1016/0957-4166(95)00326-K
  45. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; HaKumada, M. Bull. Chem. Jpn. 1980, 53, 1138. https://doi.org/10.1246/bcsj.53.1138
  46. Marr, G.; Hunt, T. J. Chem. Soc. (C) 1969, 1070.
  47. Honeychuck, R. V.; Okoroafor, M. O.; Shen, L.-H.; Brubaker, C. H., Jr.; Organometallics 1986, 5, 482. https://doi.org/10.1021/om00134a015
  48. Doyle, M. P.; Bagheri, V.; Wandless, T. J.; 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
  49. J. Am. Chem. Soc. v.112 Doyle, M.P;Bagheri, V;Wandless, T.J;Harn, N.K;Brinker, D.A;Ealge, C.T;Loh, K.L https://doi.org/10.1021/ja00161a040

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