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Sparteine as a Chiral Ligand for Asymmetric Catalysis

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Book cover Chiral Diazaligands for Asymmetric Synthesis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 15))

Abstract

While the use of stoichiometric amounts of sparteine and related ligands in various asymmetric reactions often lead to highly enantioselective transformations, there have been far fewer applications of sparteine to asymmetric catalysis. The aim of this review is to highlight recent advances in the field of asymmetric transformations that use sparteine as chiral auxiliary, emphasizing the use of substoichiometric or catalytic amounts of this ligand.

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References

  1. Hoppe D, Hense T (1997) Angew Chem Int Edit 36:2282

    Article  Google Scholar 

  2. Klein S, Marek I, Poisson JF, Normant JF (1995) J Am Chem Soc 117:8853

    Article  Google Scholar 

  3. (a) Norsikian S, Marek I, Poisson JF, Normant JF (1997) J Org Chem 62:4898, (b) Norsikian S, Marek I, Klein S, Poisson JF, Normant JF (1999) Chem Eur J 5:2055, (c) Majumdar S, De Meijere A, Marek I (2002) Synlett 423

    Google Scholar 

  4. Lautens M, Gajda C, Chiu P (1993) J Chem Soc Chem Commun 15:1193

    Article  Google Scholar 

  5. Amurrio D, Khan K, Kundig EP (1996) J Org Chem 61:2258

    Article  Google Scholar 

  6. Suzuka T, Ogasawara M, Hayashi T (2002) J Org Chem 67:3355

    Article  PubMed  Google Scholar 

  7. Asano Y, Iida A, Tomioka K (1997) Tetrahedron Lett 38:8973

    Article  Google Scholar 

  8. Xu F, Tillyer RD, Tschaen DM, Grabowski EJJ, Reider PJ (1998) Tetrahedron Asymmetry 9:1651

    Article  Google Scholar 

  9. Denmark SE, Nakajima N, Nicaise OJC (1994) J Am Chem Soc 116:8797

    Article  Google Scholar 

  10. Tomioka K, Satoh M, Taniyama D, Kanai M, Iida A (1998) Heterocycles 47:77

    Google Scholar 

  11. Jones CAG, North M (1997) Tetrahedron Asymmetry 8:3789

    Article  Google Scholar 

  12. Taniyama D, Hasegawa M, Tomioka K (1999) Tetrahedron Asymmetry 10:221

    Article  Google Scholar 

  13. Alexakis A, Amiot F (2002) Tetrahedron Asymmetry 13:2117

    Article  Google Scholar 

  14. Shintani R, Fu GC (2002) Angew Chem Int Edit 41:1057

    Article  Google Scholar 

  15. (a) Müller P, Nury P (2000) Org Lett 2:2845, (b) Müller P, Nury P, Bernardinelli G (2001) Eur J Org Chem 21:4137

    Google Scholar 

  16. Tsukazaki M, Tinkl M, Roglans A, Chapell BJ, Taylor NJ, Snieckus V (1996) J Am Chem Soc 118:685

    Article  Google Scholar 

  17. Fukuda T, Imazato K, Iwao M (2003) Tetrahedron Lett 44:7503

    Article  Google Scholar 

  18. Komine N, Wang LF, Tomooka K, Nakai T (1999) Tetrahedron Lett 40:6809

    Article  Google Scholar 

  19. Nakamura S, Nakagawa R, Watanabe Y, Toru T (2000) J Am Chem Soc 122:11340

    Article  Google Scholar 

  20. Manabe S (1997) Chem Commun 737

    Google Scholar 

  21. Tomooka K, Komine N, Nakai T (1998) Tetrahedron Lett 39:5513

    Article  Google Scholar 

  22. Hodgson DM, Lee GP (1997) Tetrahedron Asymmetry 8:2303

    Article  Google Scholar 

  23. Hodgson DM, Cameron ID (2001) Org Lett 3:441

    Article  PubMed  Google Scholar 

  24. Hodgson DM, Galano JM, Christlieb M (2003) Tetrahedron 59:9719

    Article  Google Scholar 

  25. Hodgson DM, Stent MAH, Stefane B, Wilson FX (2003) Org Biomol Chem 1:1139

    Article  PubMed  Google Scholar 

  26. Rajca A, Wang H, Bolshov P, Rajca S (2001) Tetrahedron 57:3725

    Article  Google Scholar 

  27. Zhang Y, Yeung SM, Wu H, Heller DP, Wu C, Wulff WD (2003) Org Lett 5:1813

    Article  PubMed  Google Scholar 

  28. Smrčina M, Lorenc M, Hanus V, Sedmera P, Kočovský P (1992) J Org Chem 57:1917

    Article  Google Scholar 

  29. Smrčina M, Poláková J, Vyskocyl S, Kočovský P (1993) J Org Chem 58:4534

    Article  Google Scholar 

  30. Noji M, Nakajima M, Koga K (1994) Tetrahedron Lett 35:7983

    Google Scholar 

  31. Nakajima M, Miyoshi I, Kanayama K, Hashimoto SI, Noji M, Koga K (1999) J Org Chem 64:2264

    Article  Google Scholar 

  32. Miura M, Enna M, Okuro K, Nomura M (1995) J Org Chem 60:4999

    Article  Google Scholar 

  33. Müller P, Boléa C (2001) Helv Chim Acta 84:1093

    Article  Google Scholar 

  34. Müller P, Boléa C (2002) Helv Chim Acta 85:483

    Article  Google Scholar 

  35. Müller P, Nury P (2001) Helv Chim Acta 84:662

    Article  Google Scholar 

  36. Trost BM, Dietsch TJ (1973) J Am Chem Soc 95:8200

    Article  Google Scholar 

  37. Muller D, Umbricht G, Weber B, Pfaltz A (1991) Helv Chim Acta 74:232

    Article  Google Scholar 

  38. Togni A (1991) Tetrahedron Asymmetry 2:683

    Article  Google Scholar 

  39. Kang J, Cho WO, Cho H (1994) Tetrahedron Asymmetry 5:1347

    Article  Google Scholar 

  40. Iwata T, Miyake Y, Nishibayashi Y, Uemura S (2002) J Chem Soc Perkin T 1 13:1548

    Google Scholar 

  41. Ferreira EM, Stoltz BM (2001) J Am Chem Soc 123:7725

    Article  PubMed  Google Scholar 

  42. Jensen DR, Pugsley JS, Sigman MS (2001) J Am Chem Soc 123:7475

    Article  PubMed  Google Scholar 

  43. Bagdanoff JT, Ferreira EM, Stoltz BM (2003) Org Lett 5:835

    Article  PubMed  Google Scholar 

  44. Bagdanoff JT, Stoltz BM (2004) Angew Chem Int Edit 43:353

    Article  Google Scholar 

  45. Mandal SK, Jensen DR, Pugsley JS, Sigman MS (2003) J Org Chem 68:4600

    Article  PubMed  Google Scholar 

  46. Jensen DR, Sigman MS (2003) Org Lett 5:63

    Article  PubMed  Google Scholar 

  47. Mueller JA, Jensen DR, Sigman MS (2002) J Am Chem Soc 124:8202

    Article  PubMed  Google Scholar 

  48. Mueller JA, Sigman MS (2003) J Am Chem Soc 125:7005

    Article  PubMed  Google Scholar 

  49. Ferreira EM, Stoltz BM (2002) US Patent 02 072 514

    Google Scholar 

  50. Sayyed Ali I, Sudalai A (2002) Tetrahedron Lett 43:5435

    Article  Google Scholar 

  51. Trend RM, Ramtohul YK, Ferreira EM, Stoltz BM (2003) Angew Chem Int Edit 43:2892

    Article  Google Scholar 

  52. (a) Li X, Schenkel LB, Kozlowski MC (2000) Org Lett 2:875, (b) Li X, Yang J, Kozlowski MC (2001) Org Lett 3:1137, (c) Li X, Hewgley JB, Mulrooney CA, Yang J, Kozlowski MC (2003) J Org Chem 68:5500, (d) Mulrooney CA, Li X, DiVirgilio ES, Kozlowski MC (2003) J Am Chem Soc 125:6856

    Google Scholar 

  53. (a) Dearden MJ, Firkin CR, Hermet JPR, O'Brien P (2002) J Am Chem Soc 124:11870, (b) Hermet JPR, Porter DW, Dearden MJ, Harrison JR, Koplin T, O'Brien P, Parmene J, Tyurin V, Whitwood AC, Gilday J, Smith NM (2003) Org Biomol Chem 1:3977

    Google Scholar 

  54. Phuan PW, Ianni JC, Kozlowski MC (2004) J Am Chem Soc 126:15473

    PubMed  Google Scholar 

  55. O'Brien P, Wiberg KB, Bailey WF, Hermet JP, McGrath MJ (2004) J Am Chem Soc 126:15480

    PubMed  Google Scholar 

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Authors and Affiliations

  1. Laboratoire de Chimie Organique et Médicinale, Department de Chimie, Université Catholique de Louvain, place Louis Pasteur 1, 1348, Louvain la Neuve, Belgium

    Olivier Chuzel & Olivier Riant

Authors
  1. Olivier Chuzel
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  2. Olivier Riant
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Correspondence to Olivier Riant .

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Marc Lemaire Pierre Mangeney

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Chuzel, O., Riant, O. Sparteine as a Chiral Ligand for Asymmetric Catalysis. In: Lemaire, M., Mangeney, P. (eds) Chiral Diazaligands for Asymmetric Synthesis. Topics in Organometallic Chemistry, vol 15. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136348

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