Advertisement

π-Facial Selectivity of Diels-Alder Reactions

  • Masaru Ishida
  • Satoshi Inagaki
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 289)

Abstract

Diels-Alder reaction is one of the most fundamental and important reactions for organic synthesis. In this chapter we review the studies of the π-facial selectivity in the Diels-Alder reactions of the dienes having unsymmetrical π-plane. The theories proposed as the origin of the selectivity are discussed.

Keywords

π-Facial selectivity σ/π Interaction CH/π Interaction Ciplak effect Diels-Alder reaction Electrostatic interaction Orbital mixing rule Orbital phase environment Secondary orbital interaction Steric repulsion Torsional control 

Notes

Acknowledgement

The authors thank Ms. Jane Clarkin for her English suggestions.

References

  1. 1.
    Winstein S, Shatavsky M, Norton C, Woodward RB (1955) J Am Chem Soc 77:4183CrossRefGoogle Scholar
  2. 2.
    Inagaki S, Fujimoto H, Fukui K (1976) J Am Chem Soc 98:4054CrossRefGoogle Scholar
  3. 3.
    Ishida M, Beniya Y, Inagaki S, Kato S (1990) J Am Chem Soc 112:8980CrossRefGoogle Scholar
  4. 4.
    Ishida M, Aoyama T, Beniya Y, Yamabe S, Kato S, Inagaki S (1993) Bull Chem Soc Jpn 66:3430CrossRefGoogle Scholar
  5. 5.
    Jones DW (1980) J Chem Soc Chem Commun 789Google Scholar
  6. 6.
    Ishida M, Aoyama T, Kato S (1989) Chem Lett 663Google Scholar
  7. 7.
    Macaulay JB, Fallis AG (1990) J Am Chem Soc 112:1136CrossRefGoogle Scholar
  8. 8.
    Werstiuk NH, Ma J, Macaulay JB, Falls AG (1992) Can J Chem 70:2798CrossRefGoogle Scholar
  9. 9.
    McClinton MA, Sik V (1992) J Chem Soc Perkin Trans 1:1891Google Scholar
  10. 10.
    Williamson KL, Hsu YFL (1970) J Am Chem Soc 92:7385CrossRefGoogle Scholar
  11. 11.
    Breslow R, Hoffman JM Jr, Perchonock C (1973) Tetrahedron Lett 14:3723CrossRefGoogle Scholar
  12. 12.
    Franck-Neumann M, Sedrati M (1983) Tetrahedron Lett 24:1391CrossRefGoogle Scholar
  13. 13.
    Ishida M, Kobayashi H, Tomohiro S, Wasada H, Inagaki S (1998) Chem Lett 41Google Scholar
  14. 14.
    Ishida M, Kobayashi H, Tomohiro S, Inagaki S (2000) J Chem Soc Perkin Trans 2:1625Google Scholar
  15. 15.
    Poirier RA, Pye CC, Xidos JD, Burnell DJ (1995) J Org Chem 60:2328CrossRefGoogle Scholar
  16. 16.
    Ishida M, Tomohiro S, Shimizu M, Inagaki S (1995) Chem Lett 739Google Scholar
  17. 17.
    Adam W, Jacob U, Prein MJ (1995) Chem Soc Chem Commun:839Google Scholar
  18. 18.
    Ishida M, Itakura M, Tashiro H (2008) Tetrahedron Lett 49:1804CrossRefGoogle Scholar
  19. 19.
    Halterman RL, McCarthy BA, McEvoy MA (1992) J Org Chem 57:5585CrossRefGoogle Scholar
  20. 20.
    Ishida M, Sakamoto M, Hattori H, Shimizu M, Inagaki S (2001) Tetrahedron Lett 42:3471CrossRefGoogle Scholar
  21. 21.
    Ishida M, Hirasawa S, Inagaki S (2003) Tetrahedron Lett 44:2187CrossRefGoogle Scholar
  22. 22.
    Hoffmann R, Woodward RB (1965) J Am Chem Soc 87:4388CrossRefGoogle Scholar
  23. 23.
    Ishihara K, Kondo S, Kurihara H, Yamamoto S, Ohashi S, Inagaki S (1997) J Org Chem 62:3026CrossRefGoogle Scholar
  24. 24.
    Ishihara K, Fushimi M (2008) J Am Chem Soc 130:7532CrossRefGoogle Scholar
  25. 25.
    Anh NT (1973) Tetrahedron 29:3227CrossRefGoogle Scholar
  26. 26.
    Ohwada T (1999) Chem Rev 99:1337CrossRefGoogle Scholar
  27. 27.
    Ishida M, Inagaki S (1994) Org Synth Chem 52:649Google Scholar
  28. 28.
    Tsuji M, Ohwada T, Shudo K (1998) Tetrahedron Lett 39:403CrossRefGoogle Scholar
  29. 29.
    Gleiter R, Ginsburg D (1979) Pure Appl Chem 51:1301CrossRefGoogle Scholar
  30. 30.
    Kaftory M, Peled M, Ginsburg D (1979) Helv Chim Acta 62:1326CrossRefGoogle Scholar
  31. 31.
    Ginsburg D (1983) Tetrahedron 39:2095CrossRefGoogle Scholar
  32. 32.
    Cieplak AS, Tait BD, Johnson CR (1989) J Am Chem Soc 111:8447CrossRefGoogle Scholar
  33. 33.
    Cieplak AS (1999) Chem Rev 99:1265CrossRefGoogle Scholar
  34. 34.
    Magnus P, Carins PM, Moursounidis J (1987) J Am Chem Soc 109:2469CrossRefGoogle Scholar
  35. 35.
    Coxon JM, Mcdonald DQ (1992) Tetrahedron Lett 33:651CrossRefGoogle Scholar
  36. 36.
    Werstiuk NH, Ma J (1994) Can J Chem 72:2493CrossRefGoogle Scholar
  37. 37.
    Xidos JD, Poirier RA, Burnell DJ (2000) Tetrahedron Lett 41:995CrossRefGoogle Scholar
  38. 38.
    Fisher MJ, Hehre WJ, Kahn SD, Overman LE (1988) J Am Chem Soc 110:4625CrossRefGoogle Scholar
  39. 39.
    Yadav VK, Senthil G, Babu KG, Parvez M, Reid JL (2002) J Org Chem 67:1109CrossRefGoogle Scholar
  40. 40.
    Sugimoto TK, Kobuke Y, Furukawa J (1976) J Org Chem 41:1457 and references cited in [42] and [49]Google Scholar
  41. 41.
    Freeman F (1975) Chem Rev 75:439 and references cited in [2] and [49]Google Scholar
  42. 42.
    Gleiter R, Paquette LA (1983) Acc Chem Res 16:328CrossRefGoogle Scholar
  43. 43.
    Albright TA, Burdett JK, Whangbo MH (1985) Orbital interactions in chemistry. Wiley, New YorkGoogle Scholar
  44. 44.
    Xidos JD, Poirier RA, Pye CC, Burnell DJ (1998) J Org Chem 63:105CrossRefGoogle Scholar
  45. 45.
    Robb MA, Haines WJ, Csizmadia IG (1973) J Am Chem Soc 95:42CrossRefGoogle Scholar
  46. 46.
    Letourneau JE, Wellman MA, Burnell DJ (1997) J Org Chem 62:7272CrossRefGoogle Scholar
  47. 47.
    Brown FK, Houk KN (1985) J Am Chem Soc 107:1971CrossRefGoogle Scholar
  48. 48.
    Kahn SD, Pau CF, Overman LE, Hehre WJ (1986) J Am Chem Soc 108:7381CrossRefGoogle Scholar
  49. 49.
    Kahn SD, Hehre WJ (1987) J Am Chem Soc 109:663CrossRefGoogle Scholar
  50. 50.
    Fleming I, Williams RV (1981) J Chem Soc Perkin Trans 1 684Google Scholar
  51. 51.
    Paquette LA, Vanucci C, Rogers RD (1989) J Am Chem Soc 111:5792CrossRefGoogle Scholar
  52. 52.
    Kalo J, Vogel E, Ginsburg D (1977) Tetrahedron 33:1183CrossRefGoogle Scholar
  53. 53.
    Nishio M (2005) Tetrahedron 61:6923CrossRefGoogle Scholar
  54. 54.
    Sodupe M, Rios R, Branchadell V, Nicholas T, Oliva A, Dannenberg JJ (1997) J Am Chem Soc 119:4232CrossRefGoogle Scholar
  55. 55.
    Mataka S, Ma J, Thiemann T, Rudziñski JM, Sawada T, Tashiro M (1995) Tetrahedron Lett 36:6105CrossRefGoogle Scholar
  56. 56.
    Mataka S, Ma J, Thiemann T, Mimura T, Sawada T, Tashiro M (1997) Tetrahedron 53:6817CrossRefGoogle Scholar
  57. 57.
    Naperstkow AM, Macaulay JB, Newlands MJ, Fallis AG (1989) Tetrahedron Lett 30:5077CrossRefGoogle Scholar
  58. 58.
    Treiber A, Dansette PM, Amri HE, Girault J-P, Ginderow D, Mornon J-P, Mansuy D (1997) J Am Chem Soc 119:1565CrossRefGoogle Scholar
  59. 59.
    Li Y, Thiemann T, Sawada T, Mataka S, Tashiro M (1997) J Org Chem 62:7926CrossRefGoogle Scholar
  60. 60.
    Li Y, Thiemann T, Mimura K, Sawada T, Mataka S, Tashiro M (1998) Eur J Org Chem 1841Google Scholar
  61. 61.
    Furukawa N, Zhang S, Horn E, Takahashi O, Saito S (1998) Heterocycles 47:793CrossRefGoogle Scholar
  62. 62.
    Otani T, Takayama J, Sugihara Y, Ishii A, Nakayama J (2003) J Am Chem Soc 125:8255CrossRefGoogle Scholar
  63. 63.
    Takayama J, Sugihara Y, Takayanagi T, Nakayama J (2005) Tetrahedron Lett 46:4165CrossRefGoogle Scholar
  64. 64.
    Takayama J, Fukuda S, Sugihara Y, Ishii A, Nakayama J (2003) Tetrahedron Lett 44:5159CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of EngineeringGifu UniversityGifuJapan

Personalised recommendations