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Functional Group Oriented Bond-Sets

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Elements of Synthesis Planning

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Abstract

During synthesis most skeletal bonds are made by polar bond formation in the vicinity of functional groups. The distance between the bond being formed and the functional group determines the sign of the polarity of the bond forming reaction; distance relationships from 1,1 to 1,3 are considered. When bond formation occurs between two functional groups, a mismatch in polarity may result and has to be corrected by using “umpoled” synthons.

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References

  1. E. J. Corey, X.-M. Cheng The Logic of Chemical Synthesis, J. Wiley & Sons, New York, 1989.

    Google Scholar 

  2. D. Seebach, Angew. Chem. Int. Ed. Engl. 1979, 18, 239–258. (Angew. Chem. 1979, 91, 259–278).

    Google Scholar 

  3. R. C. Larock Comprehensive Organic Transformations, Wiley-VCH, New York, 1989.

    Google Scholar 

  4. D. A. Evans, G. C. Andrews, Acc. Chem. Res. 1974, 7, 147–155

    CAS  Google Scholar 

  5. F. Serratosa Organic Chemistry in Action, 1st ed., Elsevier, Amsterdam, 1990

    Google Scholar 

  6. G. S. Zweifel, M. H. Nantz Modern Organic Synthesis: An Introduction, W. H. Freeman and Co., New York, 2007.

    Google Scholar 

  7. S. Warren Organic Synthesis: The Disconnection Approach, J. Wiley & Sons, Chichester, 1982.

    Google Scholar 

  8. E. J. Corey, Pure Appl. Chem. 1967, 14, 19–37.

    CAS  Google Scholar 

  9. W. A. Smit, A. F. Bochkov, R. Caple Organic Synthesis: The Science behind the Art, Royal Society of Chemistry, 1998, Chapt. 2.16, p. 152.

    Google Scholar 

  10. D. Seebach Organolithium Compounds in Organic Synthesis in New Applications of Organometallic Reagents in Organic Synthesis (Ed.: D. Seyferth), Elsevier, Amsterdam, 1976, pp. 1–92.

    Google Scholar 

  11. M. Braun Houben Weyl, Methoden der Organischen Chemie vol. E19d, (Ed.: M. Hanack), G. Thieme, Stuttgart, 1993, pp. 853–1138.

    Google Scholar 

  12. R. W. Stevens, T. Mukaiyama, Chem. Lett. 1985, 851–854.

    Google Scholar 

  13. R. Fernández, J. M. Lassaletta, Synlett. 2000, 1228–1240.

    Google Scholar 

  14. M. Yus, J. Ortiz, C. Najera, ARKIVOC 2002(v), 38–47.

    Google Scholar 

  15. W. C. Still, J. Am. Chem. Soc. 1978, 100, 1481–1487.

    CAS  Google Scholar 

  16. W. C. Still, C. Sreekumar, J. Am. Chem. Soc. 1980, 102, 1201–1202.

    CAS  Google Scholar 

  17. J. M. Chong, E. K. Mar, Tetrahedron Lett. 1990, 31, 1981–1984.

    CAS  Google Scholar 

  18. J. C. Stowell, Chem. Rev. 1984, 84, 409–435.

    CAS  Google Scholar 

  19. D. Hoppe, Angew. Chem., Int. Ed. Engl. 1984, 23, 932–948. (Angew. Chem. 1984, 96, 930–946).

    Google Scholar 

  20. H. Nakahira, M. Ikebe, Y. Oku, N. Sonoda, T. Fukuyama, I. Ryu, Tetrahedron 2005, 61, 3383–3392.

    CAS  Google Scholar 

  21. I. Ryu, G. Yamamura, S. Omura, S. Minakata, M. Komatsu, Tetrahedron Lett. 2006, 47, 2283–2286.

    CAS  Google Scholar 

  22. J. S. Johnson, Angew. Chem., Int. Ed. 2004, 43, 1326–1328. (Angew. Chem. 2004, 116, 1348–1350).

    CAS  Google Scholar 

  23. B. K. Banik, Eur. J. Org. Chem. 2002, 2431–2444.

    Google Scholar 

  24. H. C. Aspinall, N. Greeves, C. Valla, Org. Lett. 2005, 7, 1919–1922.

    CAS  Google Scholar 

  25. T. Wirth, Angew. Chem., Int. Ed. Engl. 1996, 35, 61–63. (Angew. Chem. 1996, 108, 65–67).

    CAS  Google Scholar 

  26. Y. Taniguchi, M. Nakahashi, T. Kuno, M. Tsuno, Y. Makioka, K. Takaki, Y. Fujiwara, Tetrahedron Lett. 1994, 35, 4111–4114.

    CAS  Google Scholar 

  27. D. S. Surry, D. R. Spring, Chem. Soc. Rev. 2006, 35, 218–225.

    CAS  Google Scholar 

  28. T. Shono, N. Kise, T. Fujimoto, A. Yamanami, R. Nomura, J. Org. Chem. 1994, 59, 1730–1740.

    CAS  Google Scholar 

  29. R. K. Dieter, S.-J. Li, N. Chen, J. Org. Chem. 2004, 69, 2867–2870.

    CAS  Google Scholar 

  30. Y.-I. Yoshida, M. Itoh, S. Isoe, J. Chem. Soc., Chem. Commun. 1993, 547–549.

    Google Scholar 

  31. Y.-I. Yoshida, Y. Ishichi, S. Isoe, J. Am. Chem. Soc. 1992, 114, 7594–7595.

    CAS  Google Scholar 

  32. J. B. Sperry, D. L. Wright, Chem. Soc. Rev. 2006, 35, 605–621.

    CAS  Google Scholar 

  33. K. Naraska, Y. Kohno, S. Shimada, Chem. Lett. 1993, 22, 125–128.

    Google Scholar 

  34. K. Otsubo, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5763–5764.

    CAS  Google Scholar 

  35. E. J. Enholm, H. Satici, A. Trivellas, J. Org. Chem. 1989, 54, 5841–5843.

    CAS  Google Scholar 

  36. G. Masson, P. Cividino, S. Py, Y. Vallée, Angew. Chem., Int. Ed. 2003, 42, 2265–2268. (Angew. Chem. 2003, 115, 2367–2370).

    CAS  Google Scholar 

  37. E. J. Corey, A. K. Ghosh, Chem. Lett. 1987, 16, 223–226.

    Google Scholar 

  38. B. B. Snider, Chem. Rev. 1996, 96, 339–363.

    CAS  Google Scholar 

  39. T. Linker, J. Prakt. Chem. 1997, 339, 488–492.

    CAS  Google Scholar 

  40. F. A. Davis, B.-C. Chen, Chem. Rev. 1992, 92, 919–934.

    CAS  Google Scholar 

  41. C. Greck, J. P. Gênet, Synlett 1997, 741–748.

    Google Scholar 

  42. P. Dembech, G. Seconi, A. Ricci, Chem. Eur. J. 2000, 6, 1281–1286.

    CAS  Google Scholar 

  43. C. D. Johnson, Acc. Chem. Res. 1993, 26, 476–482.

    CAS  Google Scholar 

  44. P. C. Wälchli, C. H. Eugster, Helv. Chim. Acta 1978, 61, 885–898.

    Google Scholar 

  45. S. R. Angle, R. M. Henry, J. Org. Chem. 1998, 63, 7490–7497.

    CAS  Google Scholar 

  46. Y. Hirai, J. Watanabe, T. Nozaki, H. Yokoyama, S. Yamaguchi, J. Org. Chem. 1997, 62, 776–777.

    CAS  Google Scholar 

  47. O. Muraoka, B.-Z. Zheng, K. Okumura, G. Tanabe, T. Momose, C. H. Eugster, J. Chem. Soc., Perkin Trans. 1, 1996, 1567–1575.

    Google Scholar 

  48. B. Nader, T. R. Bailey, R. W. Franck, S. M. Weinreb, J. Am. Chem. Soc. 1981, 103, 7573–7580.

    CAS  Google Scholar 

  49. R. S. Mali, M. Pohmakotr, B. Weidmann, D. Seebach, Liebigs Ann. Chem. 1981, 2272–2284.

    Google Scholar 

  50. J. W. Labadie, D. Tueting, J. K. Stille, J. Org. Chem. 1983, 48, 4634–4642.

    CAS  Google Scholar 

  51. J. E. Baldwin, R. M. Adlington, S. H. Ramcharitar, Synlett 1992, 875–877.

    Google Scholar 

  52. P. Bakuzis, M. L. F. Bakuzis, T. F. Weingartner, Tetrahedron Lett. 1978, 19, 2371–2374.

    Google Scholar 

  53. F. Derguini, G. Linstrumelle, Tetrahedron Lett. 1984, 25, 5763–5766.

    CAS  Google Scholar 

  54. B. M. Trost, F. W. Gowland, J. Org. Chem. 1979, 44, 3448–3450.

    CAS  Google Scholar 

  55. B. Seuring, D. Seebach, Liebigs Ann. Chem. 1978, 2044–2073.

    Google Scholar 

  56. K. F. Burri, R. A. Cardone, W. Y. Chen, P. Rosen, J. Am. Chem. Soc. 1978, 100, 7069–7071.

    CAS  Google Scholar 

  57. M. Asaoka, N. Yanagida, N. Sugimura, T. Takei, Bull. Chem. Soc. Jpn. 1980, 53, 1061–1064.

    CAS  Google Scholar 

  58. E. W. Colvin, T. A. Purcell, R. A. Raphael, J. Chem. Soc., Perkin Trans. 1, 1976, 1718–1722.

    Google Scholar 

  59. H. Gerlach, K. Oertle, A. Thalmann, Helv. Chim. Acta 1977, 60, 2860–2865.

    CAS  Google Scholar 

  60. E. J. Corey, K. C. Nicolaou, T. Toru, J. Am. Chem. Soc. 1975, 97, 2287–2288.

    CAS  Google Scholar 

  61. H. J. Bestmann, R. Schobert, Angew. Chem., Int. Ed. Engl. 1985, 24, 791–792. (Angew. Chem. 1985, 97, 784–785).

    Google Scholar 

  62. H. Stetter, Angew. Chem., Int. Ed. Engl. 1976, 15, 639–647. (Angew. Chem. 1976, 88, 695–704).

    Google Scholar 

  63. P. S. Baran, M. P. DeMartino, Angew. Chem., Int. Ed. 2006, 45, 7083–7086. (Angew. Chem. 2006, 118, 7241–7244).

    CAS  Google Scholar 

  64. H.-Y. Jang, J.-B. Hong, D. W. C. MacMillan, J. Am. Chem. Soc. 2007, 129, 7004–7005.

    CAS  Google Scholar 

  65. K. Narasaka, N. Miyoshi, K. Iwakura, T. Okauchi, Chem. Lett. 1989, 18, 2169–2172.

    Google Scholar 

  66. C.-G. Yang, N. W. Reich, Z. Shi, C. He, Org. Lett. 2005, 7, 4553–4556.

    CAS  Google Scholar 

  67. T. A. Hase, A. Ourila, C. Holmberg, J. Org. Chem. 1981, 46, 3137–3139.

    CAS  Google Scholar 

  68. J.-E. Bäckval, Bull. Soc. Chim. Fr. 1987, 665–670.

    Google Scholar 

  69. H. H. Wasserman, J. L. Ives, Tetrahedron 1981, 37, 1825–1852.

    CAS  Google Scholar 

  70. A. Defoin, H. Fritz, G. Geffroy, G. Streith, Tetrahedron Lett. 1986, 27, 4727–4730.

    CAS  Google Scholar 

  71. D. L. Boger, M. Patel, F. Takusagawa, J. Org. Chem. 1985, 50, 1911–1916.

    CAS  Google Scholar 

  72. D. J. Dixon, S. V. Ley, D. J. Reynolds, Angew. Chem., Int. Ed. 2000, 39, 3622–3626. (Angew. Chem. 2000, 112, 3768–3772).

    CAS  Google Scholar 

  73. Y. Yamamoto, H. Yamamoto, Angew. Chem., Int. Ed. 2005, 44, 7082–7085. (Angew. Chem. 2005, 117, 7244–7247).

    CAS  Google Scholar 

  74. R. S. Garigipati, A. J. Freyer, R. R. Whittle, S. M. Weinreb, J. Am. Chem. Soc. 1984, 106, 7861–7867.

    CAS  Google Scholar 

  75. J. K. Whitesell, D. James, J. F. Carpenter, J. Chem. Soc., Chem. Commun. 1985, 1449–1450.

    Google Scholar 

  76. J.-E. Baeckvall, S. E. Byström, R. E. Nordberg, J. Org. Chem. 1984, 49, 4619–4631.

    CAS  Google Scholar 

  77. K. Kondo, M. Matsumoto, Tetrahedron Lett. 1976, 17, 4363–4366.

    Google Scholar 

  78. T. L. Gilchrist, D. A. Lingham, T. G. Roberts, J. Chem. Soc., Chem. Commun. 1979, 1089–1090.

    Google Scholar 

  79. U. M. Kempe, T. K. Das Gupta, K. Blatt, P. Gygax, D. Felix, A. Eschenmoser, Helv. Chim. Acta 1972, 55, 2187–2198.

    CAS  Google Scholar 

  80. F. Felluga, P. Nitti, G. Pitacco, E. Valentin, Tetrahedron 1989, 45, 2099–2108.

    CAS  Google Scholar 

  81. M. Miyashita, T. Yanami, A. Yoshikoshi, J. Am. Chem. Soc. 1976, 98, 4679–4681.

    CAS  Google Scholar 

  82. S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137–165.

    CAS  Google Scholar 

  83. J. A. Hyatt, P. W. Raynolds, Org. Reactions 1994, 45, 159–646.

    CAS  Google Scholar 

  84. G. R. Krow, Org. Reactions 1993, 43, 251–798.

    CAS  Google Scholar 

  85. P. C. Bulman Page, M. B. van Niel, J. C. Prodger, Tetrahedron 1989, 45, 7643–7677.

    Google Scholar 

  86. M. Yus, C. Nájera, F. Foubelo, Tetrahedron 2003, 59, 6147–6212.

    CAS  Google Scholar 

  87. A. B. Smith III, S. M. Pitram, A. M. Boldi, M. J. Gaunt, C. Sfouggatakis, W. H. Moser, J. Am. Chem. Soc. 2003, 125, 14435–14445.

    CAS  Google Scholar 

  88. A. B. Smith III, V. A. Doughty, Q. Lin, L. Zhuang, M. D. McBriar, A. M. Boldi, W. H. Moser, N. Murase, K. Nakayama, M. Sobukawa, Angew. Chem., Int. Ed. 2001, 40, 191–195. (Angew. Chem. 2001, 113, 197–201).

    CAS  Google Scholar 

  89. S. N. Goodman, E. N. Jacobsen, Angew. Chem., Int. Ed. 2002, 41, 4703–4705. (Angew. Chem. 2002, 114, 4897–4899).

    CAS  Google Scholar 

  90. J. A. R. Schmidt, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2005, 127, 11426–11435.

    CAS  Google Scholar 

  91. J. W. Kramer, E. B. Lobkovsky, G. W. Coates, Org. Lett. 2006, 8, 3709–3712.

    CAS  Google Scholar 

  92. S. E. Denmark, M. Ahmad, J. Org. Chem. 2007, 72, 9630–9634.

    CAS  Google Scholar 

  93. M. M. Jackson, C. Leverett, J. F. Toczko, J. C. Roberts, J. Org. Chem. 2002, 67, 5032–5035.

    CAS  Google Scholar 

  94. T. Ishikawa, Y. Shimizu, T. Kudoh, S. Saito, Org. Lett. 2003, 5, 3879–3882.

    CAS  Google Scholar 

  95. J. W. Bode, E. M. Carreira, J. Org. Chem. 2001, 66, 6410–6424.

    CAS  Google Scholar 

  96. A. P. Kozikowski, M. Adamczyk, J. Org. Chem. 1983, 48, 366–372.

    CAS  Google Scholar 

  97. V. Jäger, W. Schwab, V. Buss, Angew. Chem., Int. Ed. Engl. 1981, 20, 601–603. (Angew. Chem. 1981, 93, 576–578).

    Google Scholar 

  98. S. F. Martin, B. Dupre, Tetrahedron Lett. 1983, 24, 1337–1340.

    CAS  Google Scholar 

  99. Z. Hong, L. Liu, C.-C. Hsu, C.-H. Wong, Angew. Chem., Int. Ed. 2006, 45, 7417–7421. (Angew. Chem. 2006, 118, 7577–7581).

    CAS  Google Scholar 

  100. P. A. Wade, H. R. Hinney, J. Am. Chem. Soc. 1979, 101, 1319–1320.

    CAS  Google Scholar 

  101. M. Asaoka, T. Mukuta, H. Takei, Tetrahedron Lett. 1981, 22, 735–738.

    CAS  Google Scholar 

  102. S. Kanemasa, M. Nishiuchi, A. Kamimura, K. Hori, J. Am. Chem. Soc. 1994, 116, 2324–2339.

    CAS  Google Scholar 

  103. J. W. Bode, N. Fraefel, D. Muri, E. M. Carreira, Angew. Chem., Int. Ed. 2001, 40, 2082–2085. (Angew. Chem. 2001, 113, 2128–2131).

    CAS  Google Scholar 

  104. A. Fürstner, M. D. B. Fenster, B. Fasching, C. Godbout, K. Radkowski, Angew. Chem., Int. Ed. 2006, 45, 5510–5515. (Angew. Chem. 2006, 118, 5636–5641).

    Google Scholar 

  105. M. J. Gaunt, H. F. Sneddon, P. R. Hewitt, P. Orsini, D. F. Hook, S. V. Ley, Org. Biomol. Chem 2003, 1, 15–16.

    CAS  Google Scholar 

  106. L. F. Tietze, G. Kettschau, Topics Curr. Chem. 1997, 189, 1–120.

    CAS  Google Scholar 

  107. S. L. Schreiber, R. E. Claus, J. Reagan, Tetrahedron Lett. 1982, 23, 3867–3870.

    CAS  Google Scholar 

  108. J. Enda, T. Matsutani, I. Kuwajima, Tetrahedron Lett. 1984, 25, 5307–5310.

    CAS  Google Scholar 

  109. B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1979, 101, 6429–6432.

    CAS  Google Scholar 

  110. D. Seebach, P. Knochel, Helv. Chim. Acta 1984, 67, 261–283.

    CAS  Google Scholar 

  111. J. Yu, H.-S. Cho, J. R. Falck, J. Org. Chem. 1993, 58, 5892–5894.

    CAS  Google Scholar 

  112. E. P. Kündig, A. F. Cunningham jr., Tetrahedron 1988, 44, 6855–6860.

    Google Scholar 

  113. A. B. Smith III, C. M. Adams, Acc. Chem. Res. 2004, 37, 365–377.

    CAS  Google Scholar 

  114. K. Ogura, M. Suzuki, J.-I. Watanabe, M. Yamashita, H. Iida, G. I. Tsuchihashi, Chem. Lett. 1982, 11, 813–814.

    Google Scholar 

  115. P. Blatcher, J. I. Grayson, S. Warren, J. Chem. Soc., Chem. Commun. 1976, 547–549.

    Google Scholar 

  116. B. M. Trost, Y. Tamaru, J. Am. Chem. Soc. 1977, 99, 3101–3113.

    CAS  Google Scholar 

  117. O. Possel, A. M. van Leusen, Tetrahedron Lett. 1977, 18, 4229–4232.

    Google Scholar 

  118. J. P. Collman, Acc. Chem. Res. 1975, 8, 342–347.

    CAS  Google Scholar 

  119. J. E. McMurry, A. Andrus, Tetrahedron Lett. 1980, 21, 4687–4690.

    CAS  Google Scholar 

  120. G. E. Niznik, W. H. Morrison III, H. M. Walborsky, J. Org. Chem. 1974, 39, 600–604.

    CAS  Google Scholar 

  121. B. M. Trost, P. Quayle, J. Am. Chem. Soc. 1984, 106, 2469–2471.

    CAS  Google Scholar 

  122. W. L. Whipple, H. J. Reich, J. Org. Chem. 1991, 56, 2911–2912.

    CAS  Google Scholar 

  123. C. Cardellicchio, V. Fiandanese, G. Marchese, L. Ronzini, Tetrahedron Lett. 1985, 26, 3595–3598.

    CAS  Google Scholar 

  124. T. P. Meagher, L. Yet, C.-N. Hsiao, H. Shechter, J. Org. Chem. 1998, 63, 4181–4192.

    CAS  Google Scholar 

  125. M. Ashwell, W. Clegg, R. F. W. Jackson, J. Chem. Soc., Perkin Trans. 1, 1991, 897–908.

    Google Scholar 

  126. A. B. Smith III, M. O. Duffey, Synlett 2004, 1363–1366.

    Google Scholar 

  127. G. Majetich, R. Desmond, A. M. Casares, Tetrahedron Lett. 1983, 24, 1913–1916.

    CAS  Google Scholar 

  128. B. M. Trost, P. J. Bonk, J. Am. Chem. Soc. 1985, 107, 1778–1781.

    CAS  Google Scholar 

  129. S. D. Rychnovsky, D. Fryszman, U. R. Khire, Tetrahedron Lett. 1999, 40, 41–44.

    CAS  Google Scholar 

  130. J.-F. Margathe, M. Shipman, S. C. Smith, Org. Lett. 2005, 7, 4987–4990.

    CAS  Google Scholar 

  131. K. Mori, J. Heterocycl. Chem. 1996, 33, 1497–1517.

    CAS  Google Scholar 

  132. R. W. Hoffmann, B. Kemper, Tetrahedron Lett. 1982, 23, 845–848.

    CAS  Google Scholar 

  133. Y. Yamamoto, Y. Saito, K. Maruyama, Tetrahedron Lett. 1982, 23, 4959–4962.

    CAS  Google Scholar 

  134. P. G. M. Wuts, S. S. Bigelow, Synth. Commun. 1982, 12, 779–785.

    CAS  Google Scholar 

  135. H. H. Wasserman, E. H. Barber, J. Am. Chem. Soc. 1969, 91, 3674–3675.

    CAS  Google Scholar 

  136. I. R. Trehan, J. Singh, K. Ajay, J. Kaur, G. L. Kad, Indian J. Chem. 1995, 34B, 396–398.

    CAS  Google Scholar 

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    R.W. Hoffmann

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Hoffmann, R. (2009). Functional Group Oriented Bond-Sets. In: Elements of Synthesis Planning. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-79220-8_2

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