Tytuł artykułu
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Abstrakty
New N-coordinated dimethyl and di-n-butyl tin hydrides containing the oxazole moiety appeared to be useful in radical cyclizations of acyclic dihalides at the steady state. Both the hydrides were prepared in three steps starting from (-)-(S)-(2-bromophenyl)- 4-isopropyl-4,5-dihydrooxazole. The advantages of the hydrides are at least twofold. First, a resolution of the radical intermediates allows generating higher stereomeric excess than in the case of commercially available hydrides. Second, tin by-products are easily removed.
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
721--729
Opis fizyczny
Bibliogr. 21 poz., rys.
Twórcy
autor
- Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland
autor
- Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Bibliografia
- 1.Curran D.P. and DeMello N.C., J. Am. Chem. Soc., 120, 329 (1998).
- 2.Curran D.P., DeMello N.C. and Junggebauer J., J. Am. Chem. Soc., 120, 329 (1998).
- 3.Stalinski K., Polish J. Chem., 78, 611 (2004).
- 4.Curran D.P., Qi H., DeMello N.C. and Lin C.-H., J. Am. Chem. Sue., 116, 8430 (1994).
- 5.Curran D.P. and Qi H„ Helv. Chim. Acta, 79, 21 (1996).
- 6.Curran D.P. and Stalinski K., J. Org. Chem., 67, 2982 (2002).
- 7.Andrukicwicz R., Cmoch P., Gawet A. and Stalinski K., J. Org. Chem., 69, 1844 (2004).
- 8.Jastrzebski J.T.B.H. and van Koten G., Adv. Organomet. Chem., 35, 241 (1993).
- 9.Wrackmcyer B., Annul. Reports NMR Spectrosc., 38, 203 (1999).
- 10.Wrackmeyer B., Vosteen M. and Storch W.,J. Mol. Struct., 602-603, 177 (2002).
- 11.Ruzidka A., Jambor R., Brus J., Cisarova I. and Holeick J., Inorg. Chim. Acta, 323, 163 (2001) and references cited therein.
- 12.Schumann H., Wassermann B.C. and Hahn F.E., Organometallics, 11, 2803 (1992).
- 13.Daktemieks D., Dunn K., Schiesser C.H. and Tiekink E.R.T., J. Organomet. Client., 605, 209 (2000).
- 14.Schwarzkopf K., Metzger J.O., Saak W. and Pohl S., Chem. Ber./Recueil, 130, 1539 (1997).
- 15.Cmoch P., Urbanczyk-Lipkowska Z., Petrosyan A., Stępien A. and Stalinski K.,J. Mol. Struct., 733,29 (2005).
- 16.Curran D.P., Iladida S., Kim S.-Y. and Luo Z., J. Am. Chem. Soc., 121, 6607 (1999).
- 17.Clive D.L.J. and Wang J., J. Org. Chem., 67, 1192 (2002).
- 18.Peer M., de Jong J.C., Kiefer M., LangerT., Rieck H., Schell H., Sennhenn P., Sprinz J., Steinhagen H., Wiese B. and Helmchen G., Tetrahedron, 52, 7547 (1996).
- 19.Vedejs E., Duncan S.M. and Haight A.R.,7. Org. Chem. ,58,3046 (1993) and references cited therein.
- 20.Paulmier C., Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
- 21.Crich D., Jiao X.-Y„ Yao Q. and Harwood S.S.,J. Org. Chem., 61, 2368(1996).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0002-0082