General Aspects of Organocatalytic Cyclizations



Ring-forming reactions are an essential part of synthetic chemistry and allow access to a range of useful natural products and biologically important molecules. The applications of organocatalysis to the synthesis of functionalised, enantiopure structures really begins where organocatalysis itself begins; with the Hajos-Parrish reaction in the 1970s for the synthesis of steroids using proline. This chapter then will review the uses of organocatalysts in cyclization methodology – from the initial Hajos-Parrish discovery to current advances in the field.


Secondary Amine Phase Transfer Catalyst Conjugate Addition Cinchona Alkaloid Domino Reaction 
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  1. 1.
    (a) Baldwin JE (1976) J Chem Soc Chem Comm 734; (b) Baldwin JE, Cutting J, Dupont W, Kruse L, Silberman L, Thomas RC (1976) J Chem Soc Chem Comm 736; (c) Baldwin JE, Kruse LI (1977) J Chem Soc Chem Comm 233; (d) Baldwin JE, Lusch MJ (1982) Tetrahedron 38:2939Google Scholar
  2. 2.
    Zampella A, D’Auria MV, Minale L, Debitus C, Roussakis C (1996) J Am Chem Soc 118:11085CrossRefGoogle Scholar
  3. 3.
    Papageorgiou CD, Ley SV, Gaunt MJ (2003) Angew Chem Int Ed 42:828CrossRefGoogle Scholar
  4. 4.
    Bremeyer N, Smith SC, Ley SV, Gaunt MJ (2004) Angew Chem Int Ed 43:2681CrossRefGoogle Scholar
  5. 5.
    Papageorgiou CD, de Dios MA Cubillo, Ley SV, Gaunt MJ (2004) Angew Chem Int Ed 43:4641CrossRefGoogle Scholar
  6. 6.
    Kunz RK, MacMillan DWC (2005) J Am Chem Soc 127:3240CrossRefGoogle Scholar
  7. 7.
    Xie H, Zu L, Li H, Wang J, Wang W (2007) J Am Chem Soc 129:10886CrossRefGoogle Scholar
  8. 8.
    Xuan Y-N, Nie S-Z, Dong L-T, Zhang J-M, Yan M (2009) Org Lett 11:1583CrossRefGoogle Scholar
  9. 9.
    (a) Wynberg H, Staring EGJ (1982) J Am Chem Soc 104:166; (b) Wynberg H, Staring EGJ (1985) J Org Chem 50:1977Google Scholar
  10. 10.
    Cortez GS, Tennyson RL, Romo D (2001) J Am Chem Soc 123:7945CrossRefGoogle Scholar
  11. 11.
    Hodous BL, Fu GC (2002) J Am Chem Soc 124:1578CrossRefGoogle Scholar
  12. 12.
    (a) Hajos ZG, Parrish DR (1971) German Patent DE 2102623; (b) Hajos ZG, Parrish DR (1974) J Org Chem 39:1615Google Scholar
  13. 13.
    Eder U, Sauer G, Wiechert R (1971) Angew Chem Int Ed 10:496CrossRefGoogle Scholar
  14. 14.
    Clemente FR, Houk KN (2004) Angew Chem Int Ed 43:5766CrossRefGoogle Scholar
  15. 15.
    Shigehisa H, Mizutani T, Tosaki S-y, Ohshima T, Shibasaki M (2005) Tetrahedron 61:5057CrossRefGoogle Scholar
  16. 16.
    List B, Lerner RA, Barbas CF (2000) J Am Chem Soc 122:2395CrossRefGoogle Scholar
  17. 17.
    Pidathala C, Hoang L, Vignola N (2003) Angew Chem Int Ed 42:2785CrossRefGoogle Scholar
  18. 18.
    (a) Cobb AJA, Shaw DM, Ley SV (2004) Synlett 558; (b) Hartikka A, Arvidsson PI (2004) Tetrahedron: Asymm 15:1831; (c) Torii H, Nakadai M, Ishihara K, Saito S, Yamamoto H (2004) Angew Chem Int Ed 43:1983Google Scholar
  19. 19.
    Enders D, Niemeier O, Leo S (2006) Synlett 3399CrossRefGoogle Scholar
  20. 20.
    Itagaki N, Kimura M, Sugahara T, Iwabuchi Y (2005) Org Lett 7:4185CrossRefGoogle Scholar
  21. 21.
    Frisch K, Landa A, Saaby S, Jorgensen KA (2005) Angew Chem Int Ed 44:6058CrossRefGoogle Scholar
  22. 22.
    (a) Hechavarria MT, List B (2004) Angew Chem Int Ed 43:3958; For a related study see (b) Kikuchi M, Inagaki T, Nishiyama H (2007) Synlett 1075Google Scholar
  23. 23.
    Mangion IK, MacMillan DWC (2005) J Am Chem Soc 127:3696CrossRefGoogle Scholar
  24. 24.
    (a) Hayashi Y, Gotoh H, Tamura T, Yamaguchi H, Masui R, Shoji M (2005) J Am Chem Soc 127:16028Google Scholar
  25. 25.
    Fustero S, Jiménez D, Moscardó J, Catalán S, del Pozo C (2007) Org Lett 9:5283CrossRefGoogle Scholar
  26. 26.
    A related protocol has been described by Carlson EC, Rathbone LK, Collett ND, Carter RG (2008) J Org Chem 73:5155Google Scholar
  27. 27.
    Vignola N, List B (2004) J Am Chem Soc 126:450CrossRefGoogle Scholar
  28. 28.
    Fu A, List B, Thiel W (2006) J Org Chem 71:320CrossRefGoogle Scholar
  29. 29.
    Bihelovic F, Matovic R, Vulovic B, Saicic RN (2007) Org Lett 9:5063CrossRefGoogle Scholar
  30. 30.
    For the intermolecular version of this process, see Ibrahem I, Córdova A (2006) Angew Chem Int Ed 45:1952Google Scholar
  31. 31.
    For a useful review in combining transition metal catalysis and organocatalysis, see Shao Z, Zhang, H (2009) Chem Soc Rev 38:2745Google Scholar
  32. 32.
    Beeson TD, Mastracchio A, Hong J-B, Ashton K, MacMillan DW C (2007) Science 316:582CrossRefGoogle Scholar
  33. 33.
    Conrad JC, Kong J, Laforteza BN, MacMillan DWC (2009) J Am Chem Soc 131:11640CrossRefGoogle Scholar
  34. 34.
    For a contrasting report see Nicolaou KC, Reingruber R, Sarlah D, Bräse S (2009) J Am Chem Soc 131:2086Google Scholar
  35. 35.
    For a useful review see (a) Akiyama T (2007) Chem Rev 107:5744 which makes up a special issue on organocatalysis; (b) Connon SJ (2008) Chem Commun 2499Google Scholar
  36. 36.
    Taylor MS, Jacobsen EN (2004) J Am Chem Soc 126:10558CrossRefGoogle Scholar
  37. 37.
    Raheem IT, Thiara PS, Peterson EA, Jacobsen EN (2007) J Am Chem Soc 129:13404CrossRefGoogle Scholar
  38. 38.
    Kam T-S, Sim K-M (1998) Phytochemistry 47:145CrossRefGoogle Scholar
  39. 39.
    (a) Ciamician G, Plancher G (1896) Chem Ber 29:2475; (b) Jackson AH, Smith P (1968) Tetrahedron 24:2227Google Scholar
  40. 40.
    Seayad J, Seayad AM, List B (2006) J Am Chem Soc 128:1086CrossRefGoogle Scholar
  41. 41.
    Wanner MJ, van der Haas RNS, de Cuba KR, van Maarseveen JH, Hiemstra H (2007) Angew Chem Int Ed 46:7485CrossRefGoogle Scholar
  42. 42.
    Sewgobind NV, Wanner MJ, Ingemann S, de Gelder R, van Maarseveen JH, Hiemstra H (2008) J Org Chem 73:6405CrossRefGoogle Scholar
  43. 43.
    Muratore ME, Holloway CA, Pilling AW, Storer RI, Trevitt G, Dixon DJ (2009) J Am Chem Soc 131:10796CrossRefGoogle Scholar
  44. 44.
    Nodes WJ, Nutt DR, Chippindale AM, Cobb AJA (2009) J Am Chem Soc 131:16016CrossRefGoogle Scholar
  45. 45.
    (a) Gellman SH (1998) Acc Chem Res 31:173; (b) Horne WS, Gellman SH (2008) Acc Chem Res 41:1399Google Scholar
  46. 46.
    Chebib M, Johnston GAR (2000) J Med Chem 43:1427CrossRefGoogle Scholar
  47. 47.
    Marion N, Díez-González S, Nolan SP (2007) Angew Chem Int Ed 46:2988CrossRefGoogle Scholar
  48. 48.
    Enders D, Breuer K, Runsink J, Teles JJ (1996) Helv Chim Acta 79:1899CrossRefGoogle Scholar
  49. 49.
    (a) Kerr MS, de Alaniz JR, Rovis T (2002) J Am Chem Soc 124:10298; (b) de Alaniz JR, Kerr MS, Moore JL, Rovis T (2008) J Org Chem 73:2033; (c) de Alaniz JR, Rovis T (2009) Synlett 1189Google Scholar
  50. 50.
    Moore JL, Kerr MS, Rovis T (2006) Tetrahedron 62:11477CrossRefGoogle Scholar
  51. 51.
    Kerr MS, Rovis T (2004) J Am Chem Soc 126:8876CrossRefGoogle Scholar
  52. 52.
    (a) Hashimoto T, Maruoka K (2007) Chem Rev 107:5656; (b) Ooi T, Maruoka K (2007) Angew Chem Int Ed 46:4222; (c) Jew S-S, Park, H-G (2009) Chem Comm 7090Google Scholar
  53. 53.
    Bandini M, Eichholzer A, Monari M, Piccinelli F, Umani-Ronchi A (2007) Eur J Org Chem 2007:2917CrossRefGoogle Scholar
  54. 54.
    Bui T, Barbas CF (2000) Tetrahedron Lett 41:6951CrossRefGoogle Scholar
  55. 55.
    McGarraugh PG, Brenner SE (2009) Org Lett 11:5654CrossRefGoogle Scholar
  56. 56.
    Sun F-G, Huang X-L, Ye S (2009) J Org Chem 75:273CrossRefGoogle Scholar
  57. 57.
    Yang JW, Fonseca MTH, List B (2005) J Am Chem Soc 127:15036CrossRefGoogle Scholar
  58. 58.
    Enders D, Hüttl MRM, Grondal C, Raabe G (2006) Nature 441:861CrossRefGoogle Scholar
  59. 59.
    Wang Y, Han R-G, Zhao Y-L, Yang S, Xu P-F, Dixon DJ (2009) Angew Chem Int Ed 48:9834CrossRefGoogle Scholar
  60. 60.
    Córdova A, Notz W, Barbas CF (2001) J Org Chem 67:301CrossRefGoogle Scholar
  61. 61.
    Chowdari NS, Ramachary DB, Córdova A, Barbas CF (2002) Tetrahedron Lett 43:9471CrossRefGoogle Scholar
  62. 62.
    Yamamoto Y, Momiyama N, Yamamoto H (2004) J Am Chem Soc 126:5962CrossRefGoogle Scholar
  63. 63.
    Austin JF, Kim S-G, Sinz CJ, Xiao W-J, MacMillan DWC (2004) Proc Nat Acad Sci USA 101:5482Google Scholar
  64. 64.
    Jiang J, Yu J, Sun X-X, Rao Q-Q, Gong L-Z (2008) Angew Chem Int Ed 47:2458CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  1. 1.University of ReadingReadingUK

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