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Enantiomerically Pure Carbocyclic Derivatives from Sugar Allyltins

Autorzy
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The concise approach to enantiomerically pure, highly oxygenated carbobicyclic derivatives from sugar allyltins as well as the preparation of these sugar organometallics is reviewed.
Rocznik
Strony
881--901
Opis fizyczny
Bibliogr. 52 poz., rys.
Twórcy
autor
  • Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52, 01-224 Warszawa, sljar@icho.edu.pl
Bibliografia
  • 1. Brammer L.E. and Hudlicky T., Tetrahedron;Asymmetry, 9, 2011 (1998) and references therein.
  • 2. Suami T. and Ogawa S., Adv. Carbohydr. Chem., Biochem., 48,22 (1990); Gomez A.M., Danelon G.O., Valverde S. and Lopez J.C., J. Org. Chem., 63, 9626 (1998) and references therein.
  • 3. Mehta G. and Ramesh S.S., Chem. Commun., 2429 (2000); Mehta G. and Ramesh S.S., Tetrahedron Lett., 42, 1987 (2001).
  • 4. Hanessian S., Total Synthesis of Natural Products: The Chiron Aproach, Pergamon Press, New York, (1983); Fraser-Reid B., Acc. Chem. Res., 29, 57 (1996) and references therein.
  • 5. Herczegh P., Zsely M., Szilagyi L., Bajza I., Kovacs A., Batta G. and Bognar R., Cycloaddition Reactions in Organic Chemistry, 112 (ACS Symposium Series 494, Guiliano R.M. Edition 1992) and references therein.
  • 6. Pindur U., Lutz G. and Otto Ch., Chem. Rev., 93,741 (1993); Roush W.R., Koyama K., Curtin, M.L. and Moriarty K.J., J. Am. Chem. Soc., 118,7502(1996); Shiina J. and Nishiyama Sh., Tetrahedron, 59,6039 (2003).
  • 7. Jarosz S. and Fraser-Reid B. J. Org. Chem., 54,4011 (1989).
  • 8. Kozłowska E. and Jarosz S., J. Carbohydr. Chem., 13, 889 (1994).
  • 9. Farkland E., J. Chem. Soc., 2, 263 (1849).
  • 10. Pope W.J. and Peachey S.J., Proc. Chem. Soc., 19, 290 (1903).
  • 11. KuivilaH.G.,MenapaceL.W. and WarnerC.R,y. Am. Chem. Soc., 84,3584 (1962); Kuivila H.G.,Adv Organomet. Chem., 1,47 (1964).
  • 12. Barton D.H.R. and McCombie S.W., J. Chem. Soc., Perkin Trans. 1, 1574 (1975); Barton D.H.R. and Motherwell W.B., in Organic Synthesis Today and Tomorrow, (Trost B.M. and Hutchinson C.R. Eds, Pergamon, Oxford, 1981).
  • 13. Giese B., “Radicals in Organic Synthesis: Formation of a Carbon-Carbon Bond', Pergamon Press, New York (1986); Pereyre M., Quintard J.-P., Rahm A., “Tin in Organic Synthesis", Butterworth: Londop (1987); Mikołajczyk M., Drabowicz J. and Kiełbasiński P. inHouben-Weyl, Methods in Organic Chem¬istry, vol. E21, chapter D10; Thomas E.J., in Houben-Weyl, Methods in Organic Chemistry, vol. E21, p. 1508; Davies A.L. "Organotin Chemistry", VCH, Weinheim, New York (1997); see also: Encyclope¬dia of ReagentsforQrganic Synthesis (Wiley & Sons Ed. 1995; Editor-in-Chief, Paquette, L.), vol 7, pp. 5000 - 5039 and references therein.
  • 14. Sato T„ Synthesis, 259 (1990).
  • 15. Jarosz S. and Kozłowska E., Polish J. Chem., 72, 815 (1998).
  • 16. Jarosz S. and Zamojski A., Curr. Org. Chem., 7,13 (2003).
  • 17. Gielen M., Acc. Chem. Res., 6, 198 (1973).
  • 18. Neumann W.P., Angew. Chem. Int. Ed. Engl., 8, 287 (1969); Kawakami K. and Kuivila H.G., J. Org. Chem., 34, 1502(1969).
  • 19. Kosugi M., Kurino K., Takayama K. and Migita T., J Organometal. Chem., 56, Cl 1 (1973).
  • 20. Grignon J., Servens C. and Pereyre M., J. Organometal. Chem., 96, 225 (1975); Keck G.E. and Yates J.B., J. Am. Chem. Soc., 104, 5829 (1982); Kosugi M., Arai H., Yoshino A. and Migita T., Chem. Lett., 795 (1978).
  • 21. Keck G.E., Enholm E.J. and Kachensky D.F., Tetrahedron Lett., 25, 1867 (1984).
  • 22. Verdone J.A., Mangravite J.A., Scarpa N.M. and Kuivila H.G., J. Am. Chem. Soc., 97, 843 (1975).
  • 23. Quintard J.P.,ElissondoB. and Pereyre M.,.J. Org. Chem., 48,1559(1983); NarutaY. and MaruyamaK., J. Chem. Soc., Chem. Comm., 1264 (1983).
  • 24. Yamamoto Y., Yatagi H., Ishihara Y., Maeda N. and Maruyama K., Tetrahedron, 40, 2239 (1984); Yamamoto Y., Acc. Chem. Res., 20, 243 (1987); Yamamoto Y. and Asao N., Chem. Rev., 93, 2207 (1993); Sumida Sh-i., OhgaM., Mitani J. and Nokami J.,J.Am. Chem.Soc., 122,1310 (2000) and references therein.
  • 25. Ueno Y. and Okawara M., J. Am. Chem. Soc., 101, 1893 (1979); Ueno Y., Aoki S. and Okawara M., J. Am. Chem. Soc., 101, 5454 (1979); Ueno Y., Sano H. and Okawara M., Synthesis, 1011 (1980).
  • 26. Ueno Y., Ohta M. and Okawara M., J. Organomet. Chem., 197, Cl (1980).
  • 27. Keck G.E., Palani A. and McHardy S.F., J. Org Chem., 59, 3113 (1994).
  • 28. Mortlock S.V. and Thomas E.J., Tetrahedron Lett., 29, 2479 (1988).
  • 29. Jarosz S., Tetrahedron, 53, 10765 (1997).
  • 30. Jarosz S., Skóra S. and Szewczyk K., Tetrahedron: Asymmetry, 11, 1997 (2000).
  • 31. Lipshutz B.H., Ellsworth E.L., Dimock S.H. and Reuter D.C., Tetrahedron Lett., 30, 2065 (1989).
  • 32. Seyferth D. and Jula T.F., J. Organometal. Chem., 66, 195 (1974); Seyferth D. and Mammarella R.E., J. Organometal. Chem., 177, 53 (1979).
  • 33. Jones C.H.W., Jones R.G., Parington P. and Roberts R.M.G., J. Organomet. Chem., 32, 201 (1971).
  • 34. Jarosz S., Szewczyk K. and Zawisza A., Tetrahedron: Asymmetry, 14, 1715 (2003).
  • 35. Jarosz S., Szewczyk K. and Zawisza A., Polish J. Chem, 77, 985 (2003).
  • 36. Marshall J.A. and Elliott L.M., J. Org. Chem., 61, 4611 (1996).
  • 37. Jarosz S., unpublished results.
  • 38. Jarosz S. and Szewczyk K. Tetrahedron Lett., 42, 3021 (2001).
  • 39. Roberts B.P. and Smits T.M., Tetrahedron Lett., 42, 137 (2001); Huyser E.S. and Garcia Z., J. Org. Chem., 27, 2716(1962).
  • 40. Jousseaume B„ Noiret N., Pereyre M. and Frances J.M., J. Chem. Soc. Chem. Comm., 739 (1992); Jousseaume B., Noiret N. and Pereyre M., Organometallics, 11, 3910 (1992).
  • 41. Krief A., Provins L. and Dumont W., Angew. Chem. Int. Ed., 38, 1946 (1999).
  • 42. Gomez A.M., Moreno E., Valverde S. and Lopez J.C., SYNLETT, 891 (2002) and references therein.
  • 43. Mach M. and Jarosz S., Polish J. Chem., 71, 936 (1997).
  • 44. Jarosz S., Kozłowska E. and Jeżewski A., Tetrahedron, 53, 10775 (1997).
  • 45. Jarosz S. and Mach M., J. Chem. Soc., Perkin Trans. 1, 3943 (1998).
  • 46. Jarosz S. and Skóra S., Tetrahedron: Asymmetry, 11, 1425 (2000).
  • 47. Jarosz S., Sżewczyk K. and Zawisza A., Tetrahedron: Asymmetry, 14,1709 (2003).
  • 48. Jarosz S., Mootoo D. and Fraser-Reid B., Carbohydr. Res., 147, 59 (1986).
  • 49. Jarosz S., Tetrahedron Lett., 34, 7655 (1994).
  • 50. Jarosz S., J. Chem. Soc., Perkin Trans. 1, 3579 (1997).
  • 51. Jarosz S. and Skóra S., Tetrahedron: Asymmetry, 11, 1433 (2000).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0024-0038
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