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Stereoselection at the Steady State within radicals - How far can we go ?

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Stereoselection at the steady state is a process, which results from a complex interplay of reaction pathways that diverge and reconverge at various points. Therefore, it can be considered as a manipulation of stereocontrol mainly by reaction topography. The advantages of this process are at least twofold: First, stereoconvergence allows the system to exceed the yield of the initial stereoconvergent event, where stereomeric transition states compete. Second, a successive resolution of the reactive intermediates by chemoselective events allows the system to generate high stereomeric excess, practically without any stereoselective competition. While illustrated with radicals, the process may prove useful in other fields of chemistry.
Słowa kluczowe
Rocznik
Strony
611--622
Opis fizyczny
Bibliogr. 36 poz., rys.
Twórcy
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, stalinsk@icho.edu.pl
Bibliografia
  • 1. Curran D.P., Giese B. and Porter N.A., Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications, VCH: Weinheim, (1996).
  • 2. Eliel L. and Wilen S., Stereochemistry of Organic Compounds, Wiley-Interscience: NY, (1994).
  • 3. Curran D.P., Geib S.J. and Lin C.-H., Tetrahedron Asymmetry, 5, 199 (1994).
  • 4. Curran D.P., Shen W., Zhang J.C., Geib S.J. and Lin C.-H., Heterocycles, 37,1773 (1994).
  • 5. Curran D.P. and DeMello N.C., J. Am. Chem. Soc., 120, 329 (1998).
  • 6. Curran D.P., DeMello N.C. and Junggebauer J., J Am. Chem. Soc., 120, 342 (1998).
  • 7. Fischli A., Klaus M., Mayer H., Schonholzer P. and Rilegg R, Helv. Chim. Acta, 58, 564 (1975).
  • 8. Harada T., Shintani T. and Oku A., J. Am. Chem. Soc., 117, 12346 (1995).
  • 9. Davis A.P..Angew. Chem., Int. Ed. Engl., 36, 591 (1997).
  • 10. Generation of the diradical via abstraction of the remaining halogen can be neglected, because it is a rare event. Moreover, it is a radical-radical reaction and it should provide coupling and disproportionation products rather than diradicals.
  • 11. Porter N.A., Giese B. and Curran D.P., Acc. Chem. Res., 24, 296 (1991).
  • 12. Wipf P. and Kim Y., Tetrahedron Lett., 33, 5477 (1992).
  • 13. Beckwith A.L.J., Easton C.J., Lawrence T. and Serelis A.K,,Aust. J. Chem., 36, 545 (1983).
  • 14. Broeker J.L. and Houk K.N.,y. Org. Chem., 56, 3651 (1991).
  • 15. Curran D.P., Qi H., DeMello N.C. and Lin C.-H., J. Am. Chem. Soc., 116, 8430 (1994) and references cited therein.
  • 16. Ueno Y., Chino K., Watanabe M., Moriya O. and Okawara M., J. Chem. Soc., Perkin Trans. 1, 1351 (1986) and references cited therein.
  • 17. Stork G., Bull. Soc. Chim. Fr., 127, 675 (1990) and references cited therein.
  • 18. Villar F., Equey O. and Renaud P., Organic Letters, 2, 1061 (2000).
  • 19. Villar F., Andrey O. and Renaud P., Tetrahedron Lett., 40, 3375 (1999).
  • 20. Sugimura T., Goto S.-I., Koguro K, Futagawa T., Misaki S., Morimoto Y., Yasuoka N. and Tai A., Tetrahedron Lett., 34, 505 (1993).
  • 21. Sugimura T., Koguro K. and Tai A., Tetrahedron Lett., 34, 509 (1993).
  • 22. Birch A., Massay-Westropp R and Wright S.E., Aust. J. Chem., 6, 385 (1953).
  • 23. Nogradi M., Stereoselective Synthesis, VCH: NY (1996).
  • 24. Curran D.P. and Qi H., Helv. Chim. Acta, 79, 21 (1996).
  • 25. Curran D.P. and Staliński K., J. Org. Chem., 67, 2982 (2002).
  • 26. Reversible iodine transfer does not seem to play a role when diiodides were used as precursors, see: Newcomb M., Sanchez R.M. and Kaplan J., J. Am. Chem. Soc., 109, 1195 (1987).
  • 27. Magnusson S.R., Tetrahedron, 51, 2167 (1995) and references cited therein.
  • 28. Andrukiewicz R., Cmoch P., Gawel A. and Staliński K., J. Org. Chem., (in press).
  • 29. Lord M.D., Negri J.T. and Paquette L.A., J. Org. Chem., 60, 191 (1995).
  • 30. Trost B.M. and Li Am. Chem. Soc., 116, 10819 (1994).
  • 31. Bartlett PA., Asymmetric Synthesis, Morrison J.D.; Ed.; Acad. Press: NY 3, 411 (1984).
  • 32. Lee E., Jeong E.J., Kang E.J., Sung L.T. and Hong S.K., J. Am. Chem. Soc., 123, 10131 (2001).
  • 33. Crich D., Jiao X-Y., Yao Q. and Harwood J.S., J. Org. Chem., 61,2368 (1996).
  • 34. Daktemieks D. and Schiesser C.H., Aust. J. Chem., 54, 89 (2001) and references cited therein.
  • 35. Several chiral tin hydrides have already been synthesized, see ref. 33.
  • 36. Recycling of the tin halide products to tin hydrides is well precedent, see: Stork G. and Sher P.M., J. Am. Chem. Soc., 108, 303 (1986).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0024-0008
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