PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Synthesis of Silylated Alkylboronic Acids and Esters via Hydroboration of Allylic and Vinylic Trimethylsilanes

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Representative allylic trimethylsilanes and isopropenyltrimethylsilane were hydroborated with dichloroborane, and the products were transformed into the corresponding borgtrimethylsilylboronates. Synthesis of 2-trimethyl silylethyl boronic acid and its diethyl ester via hydroboration of trimethylvinylsilane with diisopinocampheylborane, followed by liberation of a-pinene is described
Rocznik
Strony
1587--1594
Opis fizyczny
Bibliogr. 44 poz., rys.
Twórcy
autor
Bibliografia
  • l. Suzuki A. and Brown H.C., Organie Syntheses via Boranes, vol. 3, Suzuki Coupling, Aldrich Chemical Company, Milwaukee, WI, 2003.
  • 2. Miyaura N., Metal-Catalyzed Cross-Coupling Rreactions, de Meijere A. and Diederich F. Eds.,Wiley-VCH, Weinheim 2004, vol. l, p. 41.
  • 3. Matteson D.S., Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995.
  • 4. Matteson D.S., in Boronic Acids, Hall D.G. Ed., Wiley-VCH, Weinheim, 2005, p. 305.
  • 5. Corey EJ. and Helal C.J., Angew. Chem. Int. Ed. Engl., 37, 1986 (1998).
  • 6. Morill C. and Grubbs R.H., J. Org. Chem., 68, 6031 (2003).
  • 7. Njardarson J.T., Biswas K. and Danishefsky S.J., Chem. Commun., 2759 (2002).
  • 8.   MiyauraN., in Houben-Weyl Science of Synthesis, vol. 6, Kaufmann D.E. and Matteson D.S. Eds., G.Thieme, Stuttgart, 2005, p. 257.
  • 9.   Boronic Acids, Hall D.G. Ed., Wiley-VCH, Weinheim, 2005.
  • 10.  Yang W, Gao X. and Wang B., in Boronic Acids, Hali D.G., Ed., Wiley-VCH, Weinheim, 2005, p. 481.
  • 11.  Abu Ali H., Dembitsky V.M. and Srebnik M., Contemporary Aspects of Boron: Chemistry and Biological Applications, Elsevier, Amsterdam, 2005.
  • 12.  Marciniec B., Pietraszuk C., Kownacki I. and Zaidlewicz M., Comprehensive Organic Functional Group Transformations II, Katritzky A.R. and Taylor R.J.K., Eds., vol. 2, Ramsden C., Ed., Elsevier, Amsterdam, 2005, p. 942.
  • 13.  Murphy P.J., in Houben-Weyl Science of Synthesis, vol. 6, Kaufmann D.E., Matteson D.S. Eds., G.Thieme, Stuttgart, 2005, p. 893.
  • 14.  Bhat N.G. and Garza A., Tetrahedron Lett., 44, 6833 (2003).
  • 15.  Jankowska M., Marciniec B., Pietraszuk C., Cytarska J. and Zaidlewicz M., Tetrahedron Lett., 45,6618 (2004).
  • 16.  Jankowska M., Pietraszuk C., Marciniec B. and Zaidlewicz M., Synlett., 1695 (2006).
  • 17.  Brown H.C. and Zaidlewicz M., Organie Syntheses via Boranes, vol. 2, Recent Developments, Aldrich Chemical Company, Milwaukee, WI, 2001.
  • 18.  Molander G. and Figueroa R., Aldrichimica Acta, 38, No 2, 49 (2005).
  • 19.  Chemler J., Trauner D. and Danishefsky S.J., Angew. Chem. Int. Ed., 40, 4544 (2001).
  • 20.  Kataoka N., Shelby Q., Stambuli J.P. and Hartwig J.F., J. Org. Chem., 67, 5553 (2002).
  • 21.  Zou G., Reddy Y.K. and Falck J.R., Tetrahedron Len., 42, 7213 (2001).
  • 22.  Molander G.A. and Yun C.-S., Tetrahedron, 58, 1465 (2002).
  • 23.  Suginome M. and Ito Y., Chem. Rev., 100, 3221 (2000).
  • 24.  Soderquist J.A. and Brown H.C., J. Org. Chem., 45, 3571 (1980).
  • 25.  Brown H.C. and Rangaishenvi M.Y., Chemistry and Technology of Silicon and Tin, Das K. Ed., Oxford University Press, Oxford 1992, p. 3.
  • 26.  Bhat N.G. and Aguirre C.P., Tetrahedron Lett., 41, 8027 (2000).
  • 27.  Ohmura T., Yamamoto Y. and MiyauraN., J. Am. Chem. Soc., 122, 4990 (2000).
  • 28.  Pereira S. and Srebnik M., Organometallics, 14, 3127 (1995).
  • 29.  Crudden C.M. and Edwards D., Eur. J. Org. Chem., 4695 (2003).
  • 30.  Crudden C.M., Hleba Y.B. and Chen A.C., J. Am. Chem. Soc., 126, 9200 (2004).
  • 31. HassnerA. and Soderquist J.A., .7 Organomet. Chem., 131, Cl (1977).
  • 32. Saundararajan R. and Matteson D.S., Organometallics, 14, 4157 (1995).
  • 33.  Brown H.C. and Racherla U.S., J. Org. Chem., 51, 895 (1986).
  • 34.  Brown H.C., Jadhav P.K. and Desai M.C., J. Am. Chem. Soc., 104, 4303 (1982).
  • 35.  Brown H.C. and Ravindran N., Inorg. Chem., 16, 2938 (1977).
  • 36.  Kinberger K. and Siebert W, Z Naturforsch., B, 30, 55 (1975).
  • 37.  Brown H.C., Singaram B. and Cole T.E., J. Am. Chem. Soc., 107, 460 (1985).
  • 38.  Cole T.E., Bakshi R.H., Srebnik M., Singaram B. and Brown H.C., Organometallics, 5, 203 (1986).
  • 39.  Brown H.C. and Rangaishenvi M., J. Organomet. Chem., 358, 15 (1988).
  • 40. Andersen D.G., Rankin D.W.H., Robertson H.E., Frazao C.M.F. and Schmidbaur H., Chem. Ber., 122, 2213(1989).
  • 41.  Dubac J., Laporterie A., Iloughmane H., Pillot J.P., Deleris G. and Dunogues J., J. Organomet. Chem.,281,149(1985).
  • 42.  Meager T.P. and Schechter H., J. Org. Chem., 63, 4193 (1998).
  • 43.  Brown H.C., Organic Syntheses via Boranes, J. Wiley, New York, 1975, p. 18.
  • 44.  Brown H.C. and Joshi N.N., J. Org. Chem., 53, 4059 (1988).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ6-0019-0038
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.