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Iterative Synthesis in Organic Chemistry

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Dendrimers

Part of the book series: Topics in Current Chemistry ((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.

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References

  1. Newkome GR, Moorefield CN, Vögtle F (1996) Dendritic Molecules, 1st edn. VCH, Weinheim

    Google Scholar 

  2. Schneider HJ (1991) Lexikon der Informatik und Datenverarbeitung, 3rd edn. Oldenbourg München, Wien

    Google Scholar 

  3. IBM (1985) Fachausdrücke der Informationsverarbeitung. C H Beck, Nördlingen

    Google Scholar 

  4. Voet D, Voet JG, Maelicke A (ed), Müller-Esterl W (ed) (1992) Biochemie. VCH, Weinheim

    Google Scholar 

  5. Wahil SJ, Stoops JK, Joshi VC (1983) Ann Rev Biochem 52:568

    Google Scholar 

  6. Sun S, Harrison P (1994) J Chem Soc, Chem Commun 2235

    Google Scholar 

  7. Merrifield RB (1963) J Am Chem Soc 85:2149

    Article  CAS  Google Scholar 

  8. Merrifield RB (1969) Adv Enzymol 32:221

    CAS  Google Scholar 

  9. Bayer E (1991) Angew Chem 103:117

    Article  CAS  Google Scholar 

  10. Bayer E (1991) Angew Chem Int Ed Engl 30:113

    Article  Google Scholar 

  11. Douglas SP, Whitfield DM, Kerpinsky JJ (1991) J Am Soc 113:5095

    Article  CAS  Google Scholar 

  12. Danishefsky SJ, McClure KF, Randolph JT, Ruggeri RB (1993) Science 260:1307

    Article  CAS  Google Scholar 

  13. Gassen HG, Lang A (eds) (1982) Chemical and enzymatic synthesis of gene fragments. VCH, Weinheim

    Google Scholar 

  14. Beaucage SL, Iyer RP (1992) Tetrahedron 48:2223

    Article  CAS  Google Scholar 

  15. Cho CY, Moran EJ, Cherry SR, Stephans JC, Fodor SPA, Adams CL, Sundaram A, Jacobs JW, Schultz PG (1991) Science 251:767

    Article  Google Scholar 

  16. Burgess K, Limthicum DS, Shin H (1995) Angew Chem 107:975

    Article  Google Scholar 

  17. Burgess K, Limthicum DS, Shin H (1995) Angew Chem Int Ed Engl 34:907

    Article  CAS  Google Scholar 

  18. Fodor SPA (1993) Science 261:1303

    Article  Google Scholar 

  19. Früchtel JS, Jung G (1996) Angew Chem 108:19

    Article  Google Scholar 

  20. Früchtel JS, Jung G (1996) Angew Chem Int Ed Engl 35:17

    Article  Google Scholar 

  21. Jung G (ed) (1996) Peptide and nonpeptide libraries. VCH, Weinheim

    Google Scholar 

  22. Buhleier E, Wehner W, Vögtle F (1978) Synthesis 155

    Google Scholar 

  23. Vogel E, Deger HM, Sombroek J, Palm J, Wagner A, Lex J (1980) Angew Chem 1:43

    Article  Google Scholar 

  24. Vogel E, Deger HM, Sombroek J, Palm J, Wagner A, Lex J (1980) Angew Chem Int Ed Engl 19:41

    Article  Google Scholar 

  25. Newkome GR, Yao Z-Q, Baker GR, Gupta VK (1985) J Org Chem 50:2003

    Article  CAS  Google Scholar 

  26. Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P ( 1985) Polym J 17:117

    Article  CAS  Google Scholar 

  27. de Gennes PG, Hervet HJ (1983) Phys Lett (Paris) 44:51

    Google Scholar 

  28. Denkewalter RG, Kolc JF, Lukasavage WJ (1981) US Pat 4289872

    Google Scholar 

  29. Denkewalter RG, Kolc JF, Lukasavage WJ (1985) Chem Abstract 102:79,324q

    Google Scholar 

  30. Tomalia DA, Naylor AM, Goddard III WA (1990) Angew Chem 102:119

    Article  CAS  Google Scholar 

  31. Tomalia DA, Naylor AM, Goddard III WA (1990) Angew Chem Int Ed Engl 29:138

    Article  Google Scholar 

  32. Newkome GR, Moorefield CN, Baker GR, Johnson AL, Behera RK (1991 ) Angew Chem 103:1205

    Article  CAS  Google Scholar 

  33. Newkome GR, Moorefield CN, Baker GR, Johnson AL, Behera RK (1991) Angew Chem Int Ed Engl 30:1176

    Article  Google Scholar 

  34. Mekelburger H-B, Jaworek W, Vögtle F (1992) Angew Chem 104:1609

    Article  CAS  Google Scholar 

  35. Mekelburger H-B, Jaworek W, Vögtle F (1992) Angew Chem Int Ed Engl 31:1571

    Article  Google Scholar 

  36. Review: Issberner J, Moors R, Vögtle F (1994) Angew Chem 106:2507

    Article  CAS  Google Scholar 

  37. Issberner J, Moors R, Vögtle F (1994) Angew Chem Int Ed Engl 33:2413

    Article  Google Scholar 

  38. Moors R, Vögtle F (1995) Cascade molecules. In: Newkome GR (ed) Advances in dendritic macromolecules. JAI Press Inc., 2:41

    Google Scholar 

  39. Issberner J, Böhme M, Grimme S, Nieger M, Paulus W, Vögtle F (1996) Tetrahedron Assym 7:2223

    Article  CAS  Google Scholar 

  40. Issberner J, Vögtle F, De Cola L, Balzani V (1997) Chem Eur J 3:706

    Article  CAS  Google Scholar 

  41. Brabander-van den Berg EMM, Meijer EW (1993) Angew Chem 105:1370

    Article  Google Scholar 

  42. Brabander-van den Berg EMM, Meijer EW (1993) Angew Chem Int Ed Engl 32:1308

    Article  Google Scholar 

  43. Wörner C, Mülhaupt R (1993) Angew Chem 105:1367

    Article  Google Scholar 

  44. Wörner C, Mülhaupt R (1993) Angew Chem Int Ed Engl 32:1306

    Article  Google Scholar 

  45. BASF has prepared similar polyamine dendrimers in technical scale, Paulus W (1997) BASF Research Laboratory. Personal communica-tion

    Google Scholar 

  46. Issberner J, Vögtle F, Paulus W (1997) German Patent 196 21 510.2-O.Z. 0050/46935

    Google Scholar 

  47. Hawker CJ, Frechet JMJ (1990) J Chem Soc, Chem Commun 1010

    Google Scholar 

  48. Miller TM, Neenan TX (1990) Chem Mater 2:346

    Article  CAS  Google Scholar 

  49. Moore JS, Xu Z (1991) Macromolecules 24:5893

    Article  CAS  Google Scholar 

  50. Xu Z, Moore JS (1993) Angew Chem 105:1394

    Article  CAS  Google Scholar 

  51. Xu Z, Moore JS (1993) Angew Chem Int Ed Engl 32:1354

    Article  Google Scholar 

  52. Vögtle F (1992) Supramolekulare Chemie, 2nd edn Teubner, Stuttgart

    Google Scholar 

  53. Vögtle, F (1993) Supramolecular chemistry. Wiley, Chichester; translated into Japanese and Chinese

    Google Scholar 

  54. Lehn J-M (1995) Supramolecular chemistry. VCH, Weinheim

    Google Scholar 

  55. Schröder A, Mekelburger H-B, Vögtle F (1994) Top Curr Chem 172:180

    Google Scholar 

  56. Kohnke FH, Slawin AMZ, Stoddart JF, Williams DJ (1987) Angew Chem 99:941

    Article  CAS  Google Scholar 

  57. Kohnke FH, Slawin AMZ, Stoddart JF, Williams DJ (1987) Angew Chem Int Ed Engl 26:892

    Article  Google Scholar 

  58. Kohnke FH, Mathias JP, Stoddart JF (1989) Angew Chem Adv Mater 101:1129

    CAS  Google Scholar 

  59. Ashton PR, Isaacs NS, Kohnke FH, Mathias JP, Stoddart JF (1989) Angew Chem 101:1266

    Article  CAS  Google Scholar 

  60. Ashton PR, Isaacs NS, Kohnke FH, Mathias JP, Stoddart JF (1989) Angew Chem Int Ed Engl 28:1258

    Article  Google Scholar 

  61. Benkhoff J, Boese R, Klärner F-G, Wigger AE (1994) Tetrahedron Lett 35:73

    Article  CAS  Google Scholar 

  62. Klärner F-G, Benkhoff J, Boese R, Burkert U, Kamieth M, Naatz U (1996) Angew Chem 108:1195

    Article  Google Scholar 

  63. Klärner F-G, Benkhoff J, Boese R, Burkert U, Kamieth M, Naatz U (1996) Angew Chem Int Ed Engl 35:1130

    Article  Google Scholar 

  64. Graham RJ, Paquette LA (1995) J Org Chem 60:5770

    Article  CAS  Google Scholar 

  65. 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 1:3071

    Article  Google Scholar 

  66. Scherf U, Müllen K (1992) Synthesis 23

    Google Scholar 

  67. Schlüter AD (1991) Adv Mater 3:282

    Article  Google Scholar 

  68. Godt A, Enkelmann V, Schlüter AD (1989) Angew Chem 101:1704

    Article  CAS  Google Scholar 

  69. Godt A, Enkelmann V, Schlüter AD (1989) Angew Chem Int Ed Engl 28:1680

    Article  Google Scholar 

  70. Josten W, Karbach D, Nieger M, Vögtle F, Hägele K, Svoboda M, Przybylski M (1994) Chem Ber 127:767

    Article  CAS  Google Scholar 

  71. Breidenbach S, Ohren S, Vögtle F (1995) J Chem Soc Chem Commun 1237

    Google Scholar 

  72. Breidenbach S, Ohren S, Vögtle F (1996) Chem Eur J 2:832

    Article  CAS  Google Scholar 

  73. Breidenbach S (1995) PhD thesis, University of Bonn

    Google Scholar 

  74. Ohren S (1996) PhD thesis, University of Bonn

    Google Scholar 

  75. Breidenbach S, Ohren S, Herbst-Irmer R, Kotila S, Nieger M, Vögtle F (1996), Liebigs Ann:2115

    Google Scholar 

  76. Igner E, Paynter OI, Simmonds DJ, Whiting MC (1987) J Chem Soc Perkin Trans 1:2247

    Google Scholar 

  77. Zhang JS, Moore JS, Xu Z, Aguirre RA (1992) J Am Chem Soc 114:2273

    Article  CAS  Google Scholar 

  78. Schumm JS, Pearson DL, Tour JM (1994) Angew Chem 106:1145

    Article  Google Scholar 

  79. Schumm JS, Pearson DL, Tour JM (1994) Angew Chem Int Ed Engl 33:1360

    Article  Google Scholar 

  80. Review: Tour JM (1996) Chem Rev 96:537

    Article  CAS  Google Scholar 

  81. Liess P, Hensel V, Schlüter A-D (1996) Liebigs Ann 1037

    Google Scholar 

  82. Hensel V, Schlüter A-D (1997) Liebigs Ann/Recueil 303

    Google Scholar 

  83. Maddux T, Li W, Yu L (1997) JAm Chem Soc 119:844

    Article  CAS  Google Scholar 

  84. Buchta E, Geibel K (1961) Liebigs Ann 648:36

    Article  CAS  Google Scholar 

  85. Rice LM, Grogan CH (1961) J Org Chem 26:54

    Article  CAS  Google Scholar 

  86. Menger F, Ding J (1996) Angew Chem 108:2266

    Article  Google Scholar 

  87. Menger F, Ding J (1996) Angew Chem Int Ed Engl 35:2137

    Article  CAS  Google Scholar 

  88. Buchta E, Merck W (1966) Liebigs Ann 694:1

    Article  CAS  Google Scholar 

  89. Stork G, Rychnovsky SD (1987) J Am Chem Soc 109:1564

    Article  CAS  Google Scholar 

  90. Danishefsky J, Halcomb RL (1989) J Am Chem Soc 111:6661

    Article  Google Scholar 

  91. Dondoni A, Merino P (1993) Synthesis 903

    Google Scholar 

  92. Mori Y (1997) Chem Eur J 3:849

    Article  CAS  Google Scholar 

  93. Alvarez E, Candenas M-L, Pérez R, Ravelo JL, Martin JD (1995) Chem Rev 95:1953

    Article  CAS  Google Scholar 

  94. Sücrow W, Rädecker G (1988) Chem Ber 121:219

    Article  Google Scholar 

  95. For other strategies see: (a) Bindra JS, Bindra R (1975) Creativity in organic synthesis. Academic Press, New York, London

    Google Scholar 

  96. Lindberg T (ed) (1984) Strategies and tactics in organic synthesis. Academic Press, Orlando, London

    Google Scholar 

  97. Mulzer J, Altenbach H-J, Braun M, Krohn Reissig, H-U (1991) Organic synthesis highlights. VCH, Weinheim, New York, Basel, Cambridge

    Google Scholar 

  98. Wooley KL, Fréchet JMJ, Hawker CJ (1994), Angew Chem 106:123

    Article  CAS  Google Scholar 

  99. Wooley KL, Fréchet JMJ, Hawker CJ (1994) Angew Chem Int Ed Engl 33:82

    Article  Google Scholar 

  100. Zeng F, Zimmerman SC (1996) J Am Chem Soc 118:5327

    Google Scholar 

  101. 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, Tokyo

    Google Scholar 

  102. Rice LM, Freed ME, Grogan CH (1964) J Org Chem 29:2637

    Article  CAS  Google Scholar 

  103. Rice LM, Scott KR (1968) J Med Soc 11:378

    CAS  Google Scholar 

  104. Schmidt W, Vögtle F, Poetsch E (1995) Liebigs Ann: 1319

    Google Scholar 

  105. Schmidt W (1995), PhD thesis University of Bonn

    Google Scholar 

  106. Feuerbacher N, Schmidt W, Vögtle F, Poetsch E (1997) German patent office Patent application: 97129

    Google Scholar 

Download references

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© 1998 Springer Verlag Berlin Heidelberg

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Feuerbacher, N., Vögtle, F. (1998). Iterative Synthesis in Organic Chemistry. In: Dendrimers. Topics in Current Chemistry, vol 197. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-69779-9_1

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  • DOI: https://doi.org/10.1007/3-540-69779-9_1

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