Hyperbranched chiral catalysts for the asymmetric reduction of ketones with borane

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Carsten Bolm, Nadine Derrien and Andreas Seger


Abstract

Optically active dendritic amino alcohols catalyse the enantioselective borane reduction of ketones with good yields and high enantiomeric excesses.


References

  1. For a selection of general reviews, see: H.-F. Chow, T. K.-K. Mong, M. F. Nongrum and C.-W. Wan, Tetrahedron, 1998, 54, 8543 Search PubMed; G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendritic Molecules: Concepts, Syntheses, Perspectives, VCH, Weinheim, 1996 CrossRef CAS; D. A. Tomalia, A. M. Naylor and W. A. Goddard III, Angew. Chem., 1990, 102, 119 CrossRef CAS; Angew. Chem., Int. Ed. Engl., 1990, 29, 138 Search PubMed; D. A. Tomalia and H. D. Durst, Top. Curr. Chem., 1993, 165, 193 Search PubMed; J. Issberner, R. Moors and F. Vögtle, Angew. Chem., 1994, 106, 2507 CrossRef CAS; Angew. Chem., Int. Ed. Engl., 1994, 33, 2413 Search PubMed; V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26 Search PubMed; N. Ardoin and D. Astruc, Bull. Soc. Chim. Fr., 1995, 132, 875 CAS; F. Zeng and S. C. Zimmerman, Chem. Rev., 1997, 97, 1681 CrossRef CAS; ‘Dendrimers’, Top. Curr. Chem., 1998, 197 Search PubMed; M. Fischer and F. Vögtle, Angew. Chem., 1999, 111, 935 Search PubMed; Angew. Chem., Int. Ed., 1999, 38, 884 and refs. therein CrossRef CAS.
  2. J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove and G. van Koten, Nature, 1994, 372, 659 CrossRef CAS.
  3. For later examples of achiral dendritic catalysts, see: (a) C. C. Mak and H.-F. Chow, Macromolecules, 1997, 30, 1228 CrossRef CAS; (b) H.-F. Chow and C. C. Mak, J. Org. Chem., 1997, 62, 5116 CrossRef CAS; (c) M. T. Reetz, G. Lohmer and R. Schwickardi, Angew. Chem., 1997, 109, 1559 CrossRef; Angew. Chem., Int. Ed. Engl., 1997, 36, 1526 Search PubMed; (d) I. Morao and F. P. Cossío, Tetrahedron Lett., 1997, 38, 6461 CrossRef CAS; (e) N. J. Hovestad, E. B. Eggeling, H. J. Heidbüschel, J. T. B. H. Jastrzebski, U. Kragl, W. Keim, D. Vogt and G. van Koten, Angew. Chem., 1999, 111, 1559 CrossRef; Angew. Chem., Int. Ed., 1999, 38, 1655 Search PubMed.
  4. For a review on chirality in dendritic architectures, see: H. W. I. Peerlings and E. W. Meijer, Chem. Eur. J., 1997, 3, 1563 Search PubMed.
  5. H. Brunner, J. Organomet. Chem., 1995, 500, 39 CrossRef CAS; H. Brunner and S. Altmann, Chem. Ber., 1994, 127, 2285 CrossRef CAS; H. Brunner and J. Fürst, Tetrahedron, 1994, 50, 4303 CrossRef CAS; H. Brunner and G. Net, Synthesis, 1995, 423 CrossRef CAS.
  6. M. S. T. H. Sanders-Hovens, J. F. G. A. Jansen, J. A. J. M. Vekemans and E. W. Meijer, Polym. Mater. Sci. Eng., 1995, 73, 338 Search PubMed.
  7. D. Seebach, R. E. Marti and T. Hintermann, Helv. Chim. Acta, 1996, 79, 1710 CrossRef CAS; P. B. Rheiner, H. Sellner and D. Seebach, Helv. Chim Acta, 1997, 80, 2027 CrossRef CAS; P. B. Rheiner and D. Seebach, Polym. Mater. Sci. Eng., 1997, 77, 130 Search PubMed.
  8. T. Suzuki, Y. Hirokawa, K. Ohtake, T. Shibata and K. Soai, Tetrahedron: Asymmetry, 1997, 8, 4033 CrossRef CAS.
  9. S. Yamago, M. Furukawa, A. Azuma and J.-I. Yoshida, Tetrahedron Lett., 1998, 39, 3783 CrossRef CAS.
  10. C. Köllner, B. Pugin and A. Togni, J. Am. Chem. Soc., 1998, 120, 10 274 CrossRef.
  11. C. Bolm, N. Derrien and A. Seger, Synlett, 1996, 387 CrossRef CAS.
  12. (a) G. Giffels, J. Beliczey, M. Felder and U. Kragl, Tetrahedron: Asymmetry, 1998, 9, 691 CrossRef CAS; (b) J. Beliczey, G. Giffels, U. Kragl and C. Wandrey, Tetrahedron: Asymmetry, 1997, 8, 1529 CrossRef CAS; (c) M. Felder, G. Giffels and C. Wandrey, Tetrahedron: Asymmetry, 1997, 8, 1975 CrossRef CAS; (d) U. Kragl and C. Dreisbach, Angew. Chem., 1996, 108, 684; Angew. Chem., Int. Ed. Engl., 1996, 35, 642 Search PubMed; (e) U. Kragl, C. Dreisbach and C. Wandrey, Applied Homogeneous Catalysis with Organometallic Compounds, ed. B. Cornils and W. A. Herrmann, VCH, Weinheim, 1996, p. 832 Search PubMed.
  13. S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao and S. Nakahama, J. Chem. Soc., Perkin Trans. 1, 1985, 2039 RSC.
  14. S. Itsuno, M. Nakano, K. Ito, A. Hirao, M. Owa, N. Kanda and S. Nakahama, J. Chem. Soc., Perkin Trans. 1, 1985, 2615 RSC; S. Itsuno, K. Ito, T. Maruyama, N. Kanda, A. Hirao and S. Nakahama, Bull. Chem. Soc. Jpn., 1986, 59, 3329 CAS; S. Itsuno, Y. Sakurai, K. Ito, A. Hirao and S. Nakahama, Polymer, 1987, 28, 1005 CrossRef CAS; S. Itsuno, Y. Sakurai, K. Ito, T. Maruyama, S. Nakahama and J. M. J. Fréchet, J. Org. Chem., 1990, 55, 304 CrossRef CAS.
  15. C. J. Hawker and J. M. J. Fréchet, J. Am. Chem. Soc., 1990, 112, 7638 CrossRef CAS; C. Hawker and J. M. J. Fréchet, J. Chem. Soc., Chem. Commun., 1990, 1010 RSC.
  16. Details of the syntheses will be published elsewhere. See also: N. Derrien, dissertation, RWTH Aachen 1998.
  17. Reviews: E. J. Corey and C. J. Helal, Angew. Chem., 1998, 110, 2092 Search PubMed; Angew. Chem. Int. Ed., 1998, 37, 1986 CrossRef; S. Wallbaum and J. Martens, Tetrahedron: Asymmetry, 1992, 3, 1475 CrossRef; V. K. Singh, Synthesis, 1992, 605 Search PubMed.
  18. E. J. Corey, S. Shibata and R. K. Bakshi, J. Org. Chem., 1988, 53, 2861 CrossRef CAS.
  19. Soluble polymers containing 1 give comparable results; see ref. 12(a).
  20. C. Bolm, Selective Reactions of Metal-Activated Molecules, ed. H. Werner and P. Schreier, Vieweg, Braunschweig, 1998, p. 5 Search PubMed.
  21. For a recent study on the use of dendritic palladium catalysts in a membrane reactor, see N. Brinkmann, D. Giebel, G. Lohmer, M. T. Reetz and U. Kragl, J. Catal., 1999, 183, 163 Search PubMed.
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