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Stereogenic Centers and Planning of Syntheses

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Elements of Synthesis Planning

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Abstract

Isolated stereogenic centers of chiral target structures and first stereogenic centers of sequences of neighboring stereogenic centers are generated by asymmetric synthesis, or by resolution of a racemate, or acquired from the chiral pool. Sequences of neighboring stereogenic centers are generated from an initial one by methods of diastereoselective synthesis. They are frequently perceived as patterns, for the synthesis of which special methods are established.

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References

  1. G. Quinkert, H. Stark, Angew. Chem. Int. Ed. Engl. 1983, 22, 637–655. (Angew. Chem. 1983, 95, 651–669.

    Article  Google Scholar 

  2. A. Belan, J. Bolte, A. Fauve, J. G. Gourcy, H. Veschambre, J. Org. Chem. 1987, 52, 256–260.

    Article  CAS  Google Scholar 

  3. E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551–5553.

    Article  CAS  Google Scholar 

  4. P. K. Jadhav, K. S. Bhat, P. T. Perumal, H. C. Brown, J. Org. Chem. 1986, 51, 432–439.

    Article  CAS  Google Scholar 

  5. D. Hoppe, T. Hense, Angew. Chem. Int. Ed. Engl. 1997, 36, 2282–2316. (Angew. Chem. 1997, 109, 2376–2410).

    Article  CAS  Google Scholar 

  6. J. W. Scott in Asymmetric Synthesis (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, vol. 4, 1984, pp. 1–226.

    Google Scholar 

  7. K. Mori, Tetrahedron 1975, 31, 3011–3012.

    Article  CAS  Google Scholar 

  8. H. R. Schuler, K. N. Slessor, Can. J. Chem. 1977, 55, 3280–3287.

    Article  CAS  Google Scholar 

  9. B. D. Johnston, K. N. Slessor, Can. J. Chem. 1979, 57, 233–235.

    Article  CAS  Google Scholar 

  10. S. Takano, M. Yanase, M. Takahashi, K. Ogasawara, Chem. Lett. 1987, 16, 2017–2020.

    Article  Google Scholar 

  11. K. Nakamura, M. Kinoshita, A. Ohno, Tetrahedron 1995, 51, 8799–8808.

    Article  CAS  Google Scholar 

  12. A. Steinreiber, A. Stadler, S. F. Mayer, K. Faber, O. C. Kappe, Tetrahedron Lett. 2001, 42, 6283–6286.

    Article  CAS  Google Scholar 

  13. B. H. Lipshutz, J. M. Servesko, Angew. Chem., Int. Ed. 2003, 42, 4789–4792. (Angew. Chem. 2003, 115, 4937–4940).

    Article  CAS  Google Scholar 

  14. J. M. Brown in Comprehensive Asymmetric Catalysis (Eds.: E.-N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, vol. 1, 1999, pp. 121–182.

    Google Scholar 

  15. R. L. Halterman in Comprehensive Asymmetric Catalysis (Eds.: E.-N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, vol. 1, 1999, pp. 183–195.

    Google Scholar 

  16. W. Oppolzer, R. J. Mills, M. Réglier, Tetrahedron Lett. 1986, 27, 183–186.

    Article  CAS  Google Scholar 

  17. W. Oppolzer, G. Poli, Tetrahedron Lett. 1986, 27, 4717–4720.

    Article  CAS  Google Scholar 

  18. S. Rendler, M. Oestreich, Angew. Chem., Int. Ed. 2007, 46, 498–504. (Angew. Chem. 2007, 119, 504–510).

    Article  CAS  Google Scholar 

  19. D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737–1739.

    Article  CAS  Google Scholar 

  20. F. Lopez, A. J. Minnaard, B. L. Feringa, Acc. Chem. Res. 2007, 40, 179–188.

    Article  CAS  Google Scholar 

  21. W. Oppolzer, P. Dudfield, T. Stevenson, T. Godel, Helv. Chim. Acta 1985, 68, 212–215.

    Article  CAS  Google Scholar 

  22. F. E. Ziegler, A. Kneisley, Tetrahedron Lett. 1985, 26, 263–266.

    Article  CAS  Google Scholar 

  23. C. Herber, B. Breit, Angew. Chem., Int. Ed. 2005, 44, 5267–5269. (Angew. Chem. 2005, 117, 5401–5403).

    Article  CAS  Google Scholar 

  24. B. M. Trost, T. P. Klun, J. Org. Chem. 1980, 45, 4256–4257.

    Article  CAS  Google Scholar 

  25. P. Mohr, N. Waespe-Sarcevic, C. Tamm, K. Gawronska, J. K. Gawronski, Helv. Chim. Acta 1983, 66, 2501–2511.

    Article  CAS  Google Scholar 

  26. B. Cambou, A. M. Klibanov, J. Am. Chem. Soc. 1984, 106, 2687–2692.

    Article  CAS  Google Scholar 

  27. R. Rossi, A. Carpita, M. Chini, Tetrahedron 1985, 41, 627–633.

    Article  CAS  Google Scholar 

  28. P. E. Sonnet, J. Org. Chem. 1982, 47, 3793–3796.

    Article  CAS  Google Scholar 

  29. A. G. Pepper, G. Procter, M. Voyle, J. Chem. Soc., Chem. Commun. 2002, 1066–1067.

    Google Scholar 

  30. C. Arsene, S. Schulz, Org. Lett. 2002, 4, 2869–2871.

    Article  CAS  Google Scholar 

  31. W. C. Still, J. C. Barrish, J. Am. Chem. Soc. 1983, 105, 2487–2489.

    Article  CAS  Google Scholar 

  32. K. Suzuki, E. Katayama, G. Tsuchihashi, Tetrahedron Lett. 1984, 25, 2479–2482.

    Article  CAS  Google Scholar 

  33. W. C. Still, J. A. Schneider, Tetrahedron Lett. 1980, 21, 1035–1038.

    Article  CAS  Google Scholar 

  34. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207–2293.

    Article  CAS  Google Scholar 

  35. C. J. Cowden, I. Paterson, Org. React. 1997, 51, 1–200.

    CAS  Google Scholar 

  36. R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 1987, 26, 489–503. (Angew. Chem. 1987, 99, 503–517).

    Article  Google Scholar 

  37. I. Paterson, J. A. Channon, Tetrahedron Lett. 1992, 33, 797–800.

    Article  CAS  Google Scholar 

  38. I. Paterson, R. D. Tillyer, Tetrahedron Lett. 1992, 33, 4233–4236.

    Article  CAS  Google Scholar 

  39. J. A. Marshall, G. M. Schaaf, J. Org. Chem. 2001, 66, 7825–7831.

    Article  CAS  Google Scholar 

  40. O. Arjona, R. Menchaca, J. Plumet, J. Org. Chem. 2001, 66, 2400–2413.

    Article  CAS  Google Scholar 

  41. R. Stürmer, R. W. Hoffmann, Chem. Ber. 1994, 127, 2519–2526.

    Article  Google Scholar 

  42. R. W. Hoffmann, R. Stürmer, Chem. Ber. 1994, 127, 2511–2518.

    Article  CAS  Google Scholar 

  43. R. W. Hoffmann, R. Stürmer Towards Erythronolides, Efficient Synthesis of Contiguous Stereocenters in Antibiotics and Antiviral Compounds, Chemical Synthesis and Modification (Eds.: K. Krohn, H. Kirst, H. Maas), VCH Verlagsges., Weinheim, 1993, pp. 103–110.

    Google Scholar 

  44. M. Kalesse, M. Christmann, Synthesis 2002, 981–1003.

    Google Scholar 

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  1. Phillips Universität Marburg FB Chemie, Hans-Meerwein-Str., 35042, Marburg, Germany

    R.W. Hoffmann

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Hoffmann, R. (2009). Stereogenic Centers and Planning of Syntheses. In: Elements of Synthesis Planning. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-79220-8_10

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