Iterative Synthesis in Organic Chemistry

Chapter
First Online:
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 197)

Abstract

Iterative synthesis is a useful method in organic chemistry, allowing automation of reaction sequences to synthesize nano-scale molecules. This methodology has recently gained importance as it is the prevailing synthetic strategy to build up dendrimers and other supramolecular systems. Iterative pathways open up an approach to the synthesis of monodisperse oligomers or polymeric precursors. Moreover, linear aliphatic molecules constructed of identical building blocks can be assembled. This contribution gives a brief overview of iterative syntheses with emphasis on organic preparative chemistry. In order to elucidate this principle some biological and biochemical examples are given. The scope and limits of selected iterative applications are discussed and compared to other methods.

Keywords

Dendrimers linear aliphatic molecules oligophenylenes repetitive synthesis supramolecular chemistry 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Newkome GR, Moorefield CN, Vögtle F (1996) Dendritic Molecules, 1st edn. VCH, WeinheimGoogle Scholar
  2. 2.
    Schneider HJ (1991) Lexikon der Informatik und Datenverarbeitung, 3rd edn. Oldenbourg München, WienGoogle Scholar
  3. 3.
    IBM (1985) Fachausdrücke der Informationsverarbeitung. C H Beck, NördlingenGoogle Scholar
  4. 5.
    Voet D, Voet JG, Maelicke A (ed), Müller-Esterl W (ed) (1992) Biochemie. VCH, WeinheimGoogle Scholar
  5. 6.
    Wahil SJ, Stoops JK, Joshi VC (1983) Ann Rev Biochem 52:568Google Scholar
  6. 7.
    Sun S, Harrison P (1994) J Chem Soc, Chem Commun 2235Google Scholar
  7. 8.
    Merrifield RB (1963) J Am Chem Soc 85:2149CrossRefGoogle Scholar
  8. 9.
    Merrifield RB (1969) Adv Enzymol 32:221Google Scholar
  9. 10. (a)
    Bayer E (1991) Angew Chem 103:117CrossRefGoogle Scholar
  10. 10. (b)
    Bayer E (1991) Angew Chem Int Ed Engl 30:113CrossRefGoogle Scholar
  11. 11. (a)
    Douglas SP, Whitfield DM, Kerpinsky JJ (1991) J Am Soc 113:5095CrossRefGoogle Scholar
  12. 11. (b)
    Danishefsky SJ, McClure KF, Randolph JT, Ruggeri RB (1993) Science 260:1307CrossRefGoogle Scholar
  13. 12. (a)
    Gassen HG, Lang A (eds) (1982) Chemical and enzymatic synthesis of gene fragments. VCH, WeinheimGoogle Scholar
  14. 12. (b)
    Beaucage SL, Iyer RP (1992) Tetrahedron 48:2223CrossRefGoogle Scholar
  15. 13.
    Cho CY, Moran EJ, Cherry SR, Stephans JC, Fodor SPA, Adams CL, Sundaram A, Jacobs JW, Schultz PG (1991) Science 251:767CrossRefGoogle Scholar
  16. 14. (a)
    Burgess K, Limthicum DS, Shin H (1995) Angew Chem 107:975CrossRefGoogle Scholar
  17. 14. (b)
    Burgess K, Limthicum DS, Shin H (1995) Angew Chem Int Ed Engl 34:907CrossRefGoogle Scholar
  18. 15.
    Fodor SPA (1993) Science 261:1303CrossRefGoogle Scholar
  19. 16. (a)
    Früchtel JS, Jung G (1996) Angew Chem 108:19CrossRefGoogle Scholar
  20. 16. (b)
    Früchtel JS, Jung G (1996) Angew Chem Int Ed Engl 35:17CrossRefGoogle Scholar
  21. 16. (c)
    Jung G (ed) (1996) Peptide and nonpeptide libraries. VCH, WeinheimGoogle Scholar
  22. 17.
    Buhleier E, Wehner W, Vögtle F (1978) Synthesis 155Google Scholar
  23. 18. (a)
    Vogel E, Deger HM, Sombroek J, Palm J, Wagner A, Lex J (1980) Angew Chem 1:43CrossRefGoogle Scholar
  24. 18. (b)
    Vogel E, Deger HM, Sombroek J, Palm J, Wagner A, Lex J (1980) Angew Chem Int Ed Engl 19:41CrossRefGoogle Scholar
  25. 19.
    Newkome GR, Yao Z-Q, Baker GR, Gupta VK (1985) J Org Chem 50:2003CrossRefGoogle Scholar
  26. 20.
    Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P ( 1985) Polym J 17:117CrossRefGoogle Scholar
  27. 21.
    de Gennes PG, Hervet HJ (1983) Phys Lett (Paris) 44:51Google Scholar
  28. 22. (a)
    Denkewalter RG, Kolc JF, Lukasavage WJ (1981) US Pat 4289872Google Scholar
  29. 22. (b)
    Denkewalter RG, Kolc JF, Lukasavage WJ (1985) Chem Abstract 102:79,324qGoogle Scholar
  30. 23. (a)
    Tomalia DA, Naylor AM, Goddard III WA (1990) Angew Chem 102:119CrossRefGoogle Scholar
  31. 23. (b)
    Tomalia DA, Naylor AM, Goddard III WA (1990) Angew Chem Int Ed Engl 29:138CrossRefGoogle Scholar
  32. 24. (a)
    Newkome GR, Moorefield CN, Baker GR, Johnson AL, Behera RK (1991 ) Angew Chem 103:1205CrossRefGoogle Scholar
  33. 24. (b)
    Newkome GR, Moorefield CN, Baker GR, Johnson AL, Behera RK (1991) Angew Chem Int Ed Engl 30:1176CrossRefGoogle Scholar
  34. 25. (a)
    Mekelburger H-B, Jaworek W, Vögtle F (1992) Angew Chem 104:1609CrossRefGoogle Scholar
  35. 25. (b)
    Mekelburger H-B, Jaworek W, Vögtle F (1992) Angew Chem Int Ed Engl 31:1571CrossRefGoogle Scholar
  36. 25. (c)
    Review: Issberner J, Moors R, Vögtle F (1994) Angew Chem 106:2507CrossRefGoogle Scholar
  37. 25. (d)
    Issberner J, Moors R, Vögtle F (1994) Angew Chem Int Ed Engl 33:2413CrossRefGoogle Scholar
  38. 25. (e)
    Moors R, Vögtle F (1995) Cascade molecules. In: Newkome GR (ed) Advances in dendritic macromolecules. JAI Press Inc., 2:41Google Scholar
  39. 25. (f)
    Issberner J, Böhme M, Grimme S, Nieger M, Paulus W, Vögtle F (1996) Tetrahedron Assym 7:2223CrossRefGoogle Scholar
  40. 25. (g)
    Issberner J, Vögtle F, De Cola L, Balzani V (1997) Chem Eur J 3:706CrossRefGoogle Scholar
  41. 26. (a)
    Brabander-van den Berg EMM, Meijer EW (1993) Angew Chem 105:1370CrossRefGoogle Scholar
  42. 26. (b)
    Brabander-van den Berg EMM, Meijer EW (1993) Angew Chem Int Ed Engl 32:1308CrossRefGoogle Scholar
  43. 26. (c)
    Wörner C, Mülhaupt R (1993) Angew Chem 105:1367CrossRefGoogle Scholar
  44. 26. (d)
    Wörner C, Mülhaupt R (1993) Angew Chem Int Ed Engl 32:1306CrossRefGoogle Scholar
  45. 26. (e)
    BASF has prepared similar polyamine dendrimers in technical scale, Paulus W (1997) BASF Research Laboratory. Personal communica-tionGoogle Scholar
  46. 26. (f)
    Issberner J, Vögtle F, Paulus W (1997) German Patent 196 21 510.2-O.Z. 0050/46935Google Scholar
  47. 27.
    Hawker CJ, Frechet JMJ (1990) J Chem Soc, Chem Commun 1010Google Scholar
  48. 28.
    Miller TM, Neenan TX (1990) Chem Mater 2:346CrossRefGoogle Scholar
  49. 29.
    Moore JS, Xu Z (1991) Macromolecules 24:5893CrossRefGoogle Scholar
  50. 30. (a)
    Xu Z, Moore JS (1993) Angew Chem 105:1394CrossRefGoogle Scholar
  51. 30. (b)
    Xu Z, Moore JS (1993) Angew Chem Int Ed Engl 32:1354CrossRefGoogle Scholar
  52. 31. (a)
    Vögtle F (1992) Supramolekulare Chemie, 2nd edn Teubner, StuttgartGoogle Scholar
  53. 31. (b)
    Vögtle, F (1993) Supramolecular chemistry. Wiley, Chichester; translated into Japanese and ChineseGoogle Scholar
  54. 31. (c)
    Lehn J-M (1995) Supramolecular chemistry. VCH, WeinheimGoogle Scholar
  55. 32.
    Schröder A, Mekelburger H-B, Vögtle F (1994) Top Curr Chem 172:180Google Scholar
  56. 33. (a)
    Kohnke FH, Slawin AMZ, Stoddart JF, Williams DJ (1987) Angew Chem 99:941CrossRefGoogle Scholar
  57. 33. (b)
    Kohnke FH, Slawin AMZ, Stoddart JF, Williams DJ (1987) Angew Chem Int Ed Engl 26:892CrossRefGoogle Scholar
  58. 34.
    Kohnke FH, Mathias JP, Stoddart JF (1989) Angew Chem Adv Mater 101:1129Google Scholar
  59. 35. (a)
    Ashton PR, Isaacs NS, Kohnke FH, Mathias JP, Stoddart JF (1989) Angew Chem 101:1266CrossRefGoogle Scholar
  60. 35. (b)
    Ashton PR, Isaacs NS, Kohnke FH, Mathias JP, Stoddart JF (1989) Angew Chem Int Ed Engl 28:1258CrossRefGoogle Scholar
  61. 36.
    Benkhoff J, Boese R, Klärner F-G, Wigger AE (1994) Tetrahedron Lett 35:73CrossRefGoogle Scholar
  62. 37. (a)
    Klärner F-G, Benkhoff J, Boese R, Burkert U, Kamieth M, Naatz U (1996) Angew Chem 108:1195CrossRefGoogle Scholar
  63. 37. (b)
    Klärner F-G, Benkhoff J, Boese R, Burkert U, Kamieth M, Naatz U (1996) Angew Chem Int Ed Engl 35:1130CrossRefGoogle Scholar
  64. 38. (a)
    Graham RJ, Paquette LA (1995) J Org Chem 60:5770CrossRefGoogle Scholar
  65. 38. (b)
    Alder RW, Allen PR, Edwards LS, Fray GI, Fuller KE, Gore PM, Hext NM, Perry MH, Thomas AR, Turner KS (1994) J Chem Soc Perkin Trans 1:3071CrossRefGoogle Scholar
  66. 39.
    Scherf U, Müllen K (1992) Synthesis 23Google Scholar
  67. 40.
    Schlüter AD (1991) Adv Mater 3:282CrossRefGoogle Scholar
  68. 41. (a)
    Godt A, Enkelmann V, Schlüter AD (1989) Angew Chem 101:1704CrossRefGoogle Scholar
  69. 41. (b)
    Godt A, Enkelmann V, Schlüter AD (1989) Angew Chem Int Ed Engl 28:1680CrossRefGoogle Scholar
  70. 42.
    Josten W, Karbach D, Nieger M, Vögtle F, Hägele K, Svoboda M, Przybylski M (1994) Chem Ber 127:767CrossRefGoogle Scholar
  71. 43.
    Breidenbach S, Ohren S, Vögtle F (1995) J Chem Soc Chem Commun 1237Google Scholar
  72. 44.
    Breidenbach S, Ohren S, Vögtle F (1996) Chem Eur J 2:832CrossRefGoogle Scholar
  73. 45. (a)
    Breidenbach S (1995) PhD thesis, University of BonnGoogle Scholar
  74. 45. (b)
    Ohren S (1996) PhD thesis, University of BonnGoogle Scholar
  75. 46.
    Breidenbach S, Ohren S, Herbst-Irmer R, Kotila S, Nieger M, Vögtle F (1996), Liebigs Ann:2115Google Scholar
  76. 47.
    Igner E, Paynter OI, Simmonds DJ, Whiting MC (1987) J Chem Soc Perkin Trans 1:2247Google Scholar
  77. 48.
    Zhang JS, Moore JS, Xu Z, Aguirre RA (1992) J Am Chem Soc 114:2273CrossRefGoogle Scholar
  78. 49. (a)
    Schumm JS, Pearson DL, Tour JM (1994) Angew Chem 106:1145CrossRefGoogle Scholar
  79. 49. (b)
    Schumm JS, Pearson DL, Tour JM (1994) Angew Chem Int Ed Engl 33:1360CrossRefGoogle Scholar
  80. 50.
    Review: Tour JM (1996) Chem Rev 96:537CrossRefGoogle Scholar
  81. 51.
    Liess P, Hensel V, Schlüter A-D (1996) Liebigs Ann 1037Google Scholar
  82. 52.
    Hensel V, Schlüter A-D (1997) Liebigs Ann/Recueil 303Google Scholar
  83. 53.
    Maddux T, Li W, Yu L (1997) JAm Chem Soc 119:844CrossRefGoogle Scholar
  84. 54. (a)
    Buchta E, Geibel K (1961) Liebigs Ann 648:36CrossRefGoogle Scholar
  85. 54. (b)
    Rice LM, Grogan CH (1961) J Org Chem 26:54CrossRefGoogle Scholar
  86. 55. (a)
    Menger F, Ding J (1996) Angew Chem 108:2266CrossRefGoogle Scholar
  87. 55. (b)
    Menger F, Ding J (1996) Angew Chem Int Ed Engl 35:2137CrossRefGoogle Scholar
  88. 56.
    Buchta E, Merck W (1966) Liebigs Ann 694:1CrossRefGoogle Scholar
  89. 57. (a)
    Stork G, Rychnovsky SD (1987) J Am Chem Soc 109:1564CrossRefGoogle Scholar
  90. 57. (b)
    Danishefsky J, Halcomb RL (1989) J Am Chem Soc 111:6661CrossRefGoogle Scholar
  91. 57. (c)
    Dondoni A, Merino P (1993) Synthesis 903Google Scholar
  92. 58. (a)
    Mori Y (1997) Chem Eur J 3:849CrossRefGoogle Scholar
  93. 58. (b)
    Alvarez E, Candenas M-L, Pérez R, Ravelo JL, Martin JD (1995) Chem Rev 95:1953CrossRefGoogle Scholar
  94. 59.
    Sücrow W, Rädecker G (1988) Chem Ber 121:219CrossRefGoogle Scholar
  95. 60.
    For other strategies see: (a) Bindra JS, Bindra R (1975) Creativity in organic synthesis. Academic Press, New York, LondonGoogle Scholar
  96. 60. (b)
    Lindberg T (ed) (1984) Strategies and tactics in organic synthesis. Academic Press, Orlando, LondonGoogle Scholar
  97. 60. (c)
    Mulzer J, Altenbach H-J, Braun M, Krohn Reissig, H-U (1991) Organic synthesis highlights. VCH, Weinheim, New York, Basel, CambridgeGoogle Scholar
  98. 61. (a)
    Wooley KL, Fréchet JMJ, Hawker CJ (1994), Angew Chem 106:123CrossRefGoogle Scholar
  99. 61. (b)
    Wooley KL, Fréchet JMJ, Hawker CJ (1994) Angew Chem Int Ed Engl 33:82CrossRefGoogle Scholar
  100. 61. (c)
    Zeng F, Zimmerman SC (1996) J Am Chem Soc 118:5327Google Scholar
  101. 62.
    For other concepts in nanometer size architectures see: Fuhrhop J, Penzlin G (1994) Organic synthesis: concepts, methods, starting materials, 2nd rev ed. VCH, Weinheim, New York, Basel, Cambridge, TokyoGoogle Scholar
  102. 63. a)
    Rice LM, Freed ME, Grogan CH (1964) J Org Chem 29:2637CrossRefGoogle Scholar
  103. 63. b)
    Rice LM, Scott KR (1968) J Med Soc 11:378Google Scholar
  104. 64.
    Schmidt W, Vögtle F, Poetsch E (1995) Liebigs Ann: 1319Google Scholar
  105. 65.
    Schmidt W (1995), PhD thesis University of BonnGoogle Scholar
  106. 66.
    Feuerbacher N, Schmidt W, Vögtle F, Poetsch E (1997) German patent office Patent application: 97129Google Scholar

Copyright information

© Springer Verlag Berlin Heidelberg 1998

Authors and Affiliations

  1. 1.Kekulé-Institut für Organische Chemie und Biochemie der Universität BonnBonnGermany

Personalised recommendations