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Regioselective Reactions on a Chiral Substrate Controlled by the Configuration of a Chiral Catalyst

  1. Raju Ranjith Kumar,
  2. Henri B. Kagan

Article first published online: 27 JAN 2010

DOI: 10.1002/adsc.200900822

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 352, Issue 2-3, pages 231–242, February 15, 2010

Additional Information

How to Cite

Kumar, R. R. and Kagan, Henri B. (2010), Regioselective Reactions on a Chiral Substrate Controlled by the Configuration of a Chiral Catalyst. Adv. Synth. Catal., 352: 231–242. doi: 10.1002/adsc.200900822

Author Information

  1. Laboratoire de Catalyse Moléculaire, Institut de Chimie Moléculaire et des Matériaux d'Orsay (UMR CNRS 8182), Bâtiment 420, Université Paris-Sud, 91405 Orsay, France, Fax: (+33)-1-6915-4680

Publication History

  1. Issue published online: 17 FEB 2010
  2. Article first published online: 27 JAN 2010
  3. Manuscript Received: 26 DEC 2009

Funded by

  • Université Paris-Sud
  • CNRS
  • Institut des Substances Naturelles du CNRS (Gif-sur-Yvette)

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  • 1
    Asymmetric Organic Reactions, Vol. 5, Catalysis, (Ed.: J. D. Morrison), Academic Press, New York, 1985.
  • 2
    Asymmetric Catalysis in Organic Synthesis, (Ed.: R. Noyori), Wiley, New York, 1994.
  • 3
    Catalytic Asymmetric Synthesis, (Ed.: I. Ojima), 2nd edn., Wiley-VCH, New York, 2001.
  • 4
    Comprehensive Asymmetric Catalysis, Vols. I–III, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, New York, 1999.
  • 5
    Stereo-Differentiating Reactions, (Eds.: Y. Izumi, A. Tai), Kodansha, Tokyo and Academic Press, New York, 1977.
  • 6
    H. B. Kagan, J. C. Fiaud, in: Topics in Stereochemistry, (Eds.: N. L. Allinger, E. L. Eliel), Wiley, New York, 1988; Vol. 18, pp 249–330.
  • 7
    E. Vedejs, M. Jure, Angew. Chem. 2005, 117, 4040–4069; Angew. Chem. Int. Ed. 2005, 44, 3974–4001.
  • 8
    A. H. Hoveyda, M. T. Didiuk, Curr. Org. Chem. 1998, 2, 489–526.
  • 9
    J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5–26.
  • 10
    The expression enantioselective synthesis is widely used and does not always refer to a key step involving an asymmetric synthesis.[11] For example, multi-step total syntheses of natural products are commonly qualified as enantioselective because the final product has been synthesized as a single enantiomer. The expression “enantioselectivity” will be used in the present article when meaning that an achiral starting material is transformed in one step into an enantioenriched product. Often a given reaction involves several consecutive steps and one is stereodeterminating. We will not use the word “selection” in a mechanistic discussion but only when comparing the starting material to the product (see some examples in Scheme 1).
  • 11
    For the misuse of stereochemical words see:
  • 11a
    K. Mislow, Chirality 2002, 14, 126–134;
  • 11b
    E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
  • 12
    J. P. Guetté, A. Horeau, Bull. Soc. Chim. Fr. 1967, 1747–1752.
  • 13
    S. El Baba, J. C. Poulin, H. B. Kagan, Tetrahedron 1984, 40, 4275–4284.
  • 14
     
  • 14a
    C. Bolm, G. Schlingloff, K. Weickhard, Angew. Chem. 1994, 106, 1944–1946; Angew. Chem. Int. Ed. Engl. 1994, 33, 1848–1849;
  • 14b
    C. Bolm, G. Schlingloff, J. Chem. Soc. Chem. Commun. 1995, 1247–1248.
  • 15
     
  • 15a
    A. Gusso, C. Baccin, F. Pinna, G. Strukul, Organometallics 1994, 13, 3442–3451;
  • 15b
    G. Strukul, Angew. Chem. 1998, 110, 1256–1267; Angew. Chem. Int. Ed. 1998, 37, 1199–1209.
  • 16
    A. Watanabe, T. Uchida, K. Ito, T. Katsuki, Tetrahedron Lett. 2002, 43, 4481–4485.
  • 17
    H. B. Kagan, Croat. Chem. Acta 1996, 69, 669–680.
  • 18
    H. B. Kagan, Tetrahedron 2001, 57, 2449–2459.
  • 19
    T. Honda, N. Sano, K. Kanai, Heterocycles 1995, 41, 425–429.
  • 20
    S. F. Martin, M. R. Spaller, S. Liras, B. Hartmann, J. Am. Chem. Soc. 1994, 116, 4493–4494.
  • 21
    M. P. Doyle, A. B. Dyatkin, A. V. Kalinin, D. A. Ruppar, J. Am. Chem. Soc. 1995, 117, 11021–11022.
  • 22
    M. S. Visser, A. H. Hoveyda, Tetrahedron 1995, 51, 4383–4394.
  • 23
    G. Dawson, C. A. Durrant, G. G. Kirk, R. J. Whitby, R. V. H. Jones, M. C. H. Standen, Tetrahedron Lett. 1997, 38, 2335–2338.
  • 24
    S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1–31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1–30.
  • 25
    A. Horeau, H. B. Kagan, J. P. Vigneron, Bull. Soc. Chim. Fr. 1968, 3795–3797.
  • 26
    D. L. Hughes, M. Palucki, N. Yasuda, R. A. Reamer, P. J. Reider, J. Org. Chem, 2002, 67, 2762–2768, and references cited therein.
  • 27
    T. Hayashi, A. Yamamoto, Y. Ito, J. Chem. Soc. Chem. Commun. 1986, 1090–1092.
  • 28
    O. Loiseleur, M. C. Elliott, P. von Matt, A. Pfaltz, Helv. Chim. Acta 2000, 83, 2287–2294.
  • 29
    H. Daimon, R. Ogawa, S. Itagaki, I. Shimizu, Chem. Lett. 2004, 33, 1222–1223.
  • 30
    G. R. Cook, S. Sankaranarayanan, Org. Lett. 2001, 3, 3531–3533.
  • 31
    O. Jacquet, J. Y. Legros, M. Coliboeuf, J.-C. Fiaud, Tetrahedron 2008, 64, 6530–6536.
  • 32
    R. Webster, C. Böig, M. Lautens, J. Am. Chem. Soc. 2009, 131, 444–445.
  • 33
    For examples of regiodivergent kinetic resolutions of allylic epoxides see refs.[34–36]
  • 34
    F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, B. L. Feringa, Angew. Chem. 2001, 113, 956–958; Angew. Chem. Int. Ed. 2001, 40, 930–932.
  • 35
    M. Pineschi, F. Del Moro, F. Crotti, V. Di Bussolo, F. Macchia, J. Org. Chem. 2004, 69, 2099–2105.
  • 36a
    R. Millet, A. Alexakis, Synlett 2007, 435–438;
  • 36b
    R. Millet, A. Alexakis, Synlett 2008, 1797–1800.
  • 37
    A. Gansäuer, C.-A. Fan, F. Keller, J. Keil, J. Am. Chem. Soc. 2007, 129, 3484–3485.
  • 38
    M. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837–8846.
  • 39
    M. P. Doyle, S. B. Davies, E. J. May, J. Org. Chem. 2001, 66, 8112–8119.
  • 40
    C. K. Jana, A. Studer, Angew. Chem. 2007, 119, 6662–6664; Angew. Chem. Int. Ed. 2007, 46, 6542–6544.
  • 41
    K. Tanaka, G. C. Fu, J. Am. Chem. Soc. 2002, 125, 8078–8079.
  • 42
    Y. Chen, L. Deng, J. Am. Chem. Soc. 2001, 123, 11302–11303.
  • 43
    S. Zhang, C. Girard, H. B. Kagan, Tetrahedron: Asymmetry 1995, 6, 2637–2640.
  • 44
    C. Bolm, I. Schiffers, C. L. Dinter, L. Defrère, A. Gerlach, C. Raabe, Synthesis 2001, 1719–1730.
  • 45
    C. Bolm, I. Schiffers, C. L. Dinter, A. Gerlach, J. Org. Chem. 2000, 65, 6984–6991.
  • 46
    Y. Ishii, K. Osakada, T. Ikariya, M. Saburi, S. Yoshikawa, J. Org. Chem. 1986, 51, 2034–2039.
  • 47
    I. Iwasaki, T. Maki, W. Nakashima, O. Onomura, Y. Matsumura, Org. Lett. 1999, 1, 969–972.
  • 48
    C. Mazet, S. Roseblade, V. Köhler, A. Pfaltz, Org. Lett. 2006, 8, 1879–1882.
  • 49
    C. A. Lewis, S. J. Miller, Angew. Chem. 2006, 118, 5744–5747; Angew. Chem. Int. Ed. 2006, 45, 5616–5619.
  • 50
    Y. Zhao, A. W. Mitra, A. H. Hoveyda, M. L. Snapper, Angew. Chem. 2007, 119, 8623–8626; Angew. Chem. Int. Ed. 2007, 46, 8471–8474.
  • 51
     
  • 51a
    M. Tsukamoto, H. B. Kagan, Adv. Synth. Catal. 2002, 344, 453–463;
  • 51b
    M. T. Reetz, Angew. Chem. 2002, 114, 1391–1394; Angew. Chem. Int. Ed. 2002, 41, 1335–1338.
  • 52
    M. T. Reetz, M. H. Becker, H. W. Klein, D. Stöckigt, Angew. Chem. 1999, 111, 1872–1875; Angew. Chem. Int. Ed. 1999, 38, 1758–1761.
  • 53
    The oxidation of enantiomeric aryl-substituted allylic alcohols by iodosyl benzene catalyzed by a chiral Fe(III) porphyrin complex has been described.[54] There is a competition between the C[DOUBLE BOND]C epoxidation and the allylic oxidation into enone. The chemoselectivity is slightly different according to the absolute configuration of the substrate.
  • 54
    W. Adam, S. Prikhodovski, K. J. Roschmann; C. R. Saha-Möller, Tetrahedron: Asymmetry 2001, 12, 2677–2681.
  • 55
    B. Wu, J. R. Parquette, T. V. RajanBabu, Science 2009, 326, 1662.
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