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Free Radical Addition and Cyclization Reactions of [2-(4-(S)-Isopropyl-2-oxazoline)-5-phenyl]dialkyltin Hydrides

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Radical addition reactions of [2-(4-(S)-isopropyl-2-oxazoline)-5-phenyl]dibutyl and dimethyl hydrides to activated double/triple bonds took place in good yields. Triethylborane in presence of oxygen can serve as a radical initiator. Addition of stannyl radicals to N,N-(2-methoxycarbonyl-allyl)benzyl glycinate results in formation of the corresponding piperidine derivatives. The intramolecular tandem radical addition/ cyclization process can be performed in high yields and good diastereoselectivity.
Rocznik
Strony
1015--1024
Opis fizyczny
Bibliogr. 35 poz., rys.
Twórcy
autor
  • Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
autor
  • Nesmeyanow Institute of Organo-Element Compounds, Russian Academy of Sciences, Vavilow 28, 117813 Moscow, Russia
autor
  • Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
autor
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
autor
  • Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Bibliografia
  • 1.Giese B., Radicals in Organic Chemistry: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1988.
  • 2.Curran D.P., Porter N.A. and Giese B., Stereochemistry of Radical Reactions, VCH: Weinheim, New York, 1996.
  • 3.Renaud P. and Sibi M.P., Radicals in Organic Synthesis, VCH-Wiley: Weinheim, New York, 2001.
  • 4.Chopa A.B.,Koll.C., SavimM.C.,Podesta L.C. and Neumann W.P., Organometallics, A, 1036 (1985).
  • 5.Nozaki K., Oshima K. and Utimoto K., Bull. Chem. Soc. Jpn., 64, 2585 (1991).
  • 6. Connil M.-F., Jousseaume B. and Pereyre M., Organometallics, 15, 4469 (1996).
  • 7.Curran D.P., Hadida S., Kim S.-Y. and Luo Z., J. Am. Chem. Soc., 121, 6607 (1999).
  • 8.Clive D.L.J. and Wang J., J. Org. Chem., 67, 1192 (2002) and references cited therein.
  • 9.Suga S., Manabe T. and Yoshida J.-I., Chem. Commun., 1237 (1999).
  • 10.Vedejs E., Duncan S.M. and Haight A.R., J. Org. Chem., 58, 3046 (1993).
  • 11.Blumenstein M., Schwarzkopf K. and Metzger J.O., Angew. Chem., Int. Ed. Engl., 36, 235 (1997).
  • 12.Daktemieks D., Dunn K., Perchyonok V.T. and Schiesser C.H., Chem. Commun., 1665 (1999).
  • 13.Daktemieks D. and Schiesser C.H., Aust. J. Chem., 54, 89 (2001).
  • 14.Daktemieks D., Perchyonok V.T. and Schiesser C.H., Tetrahedron: Asymm., 14, 3057 (2003).
  • 15.Jastrzębski J.T.B.T. and van Koten G., Advances in Organometallic Chemistry, 35, 241 (1993).
  • 16.Blunden S.J., Cusack P.A. and Hill R., The Industrial Uses of Tin Chemicals; Royal Society of Chemistry: London 1985.
  • 17.Gielen M., Main Group Met. Chem., 17, 1 (1994).
  • 18.Schumann H., Wassermann B.C. and Hahn F.E., Organometallics, 11, 2803 (1992).
  • 19.Schwarzkopf K., Metzger J.O., Saak W. and Pohl S., Chem. Ber./Recueil, 130, 1539 (1997).
  • 20.Daktemieks D., Dunn K., Schiesser C.H. and Tiekink E.R.T., J. Organomet. Chem., 605, 209 (2000).
  • 21.Several triorganotin halides and hydrides containing the same ligand and different substituents on the tin atom have been previously reported: Jastrz?bski J.T.B.H., Wehman E., Bocrsma J., van Koten G., Goubitz K. and Heijdenrijk D,,J. Organomet. Chem., 409, 157 (1991).
  • 22.Daktemieks D., Dunn K., Schiesser C.H. and Tiekink E.R.T.,.J. Chem. Soc., Dalton Trans., 3693 (2000).
  • 23.Cmoch P., Urbanczyk-Lipkowska Z., Petrosyan A., Stępien A. and Stalinski K., J. Mol. Struct., 733,25 (2005).
  • 24.Peer M., dc 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).
  • 25.Nozaki K., Oshima K. and Utimoto K,,J. Am. Chem. Soc., 109, 2547 (1987).
  • 26.Stork G. and Mook Jr R„ J. Am. Chem. Soc., 109, 2829 (1987).
  • 27.Lee E., Ko S.B. and Jung K.W., Tetrahedron Lett., 30, 827 (1987).
  • 28.Lee E., Hur C.-U. and Park J.-H., Tetrahedron Lett., 30, 7219 (1989).
  • 29.Lee E., Hur C.-U. and Park C.M., Tetrahedron Lett., 31, 5039 (1990).
  • 30.Quintard J.-P., Degueil-Castaing M., Dumartin G., Rahm A. and Pereyre M., J. Chem. Soc., Chem Commun., 1004 (1980).
  • 31.Jung M.E. and Light L.A., Tetrahedron Lett., 38, 3851 (1982).
  • 32.For the palladium(O) catalyzed addition of alkylstannancs to acetylenic esters, see: Cochran J., Bron B.S., Terrence K.M. and Phillips H.K., Tetrahedron Lett. ,31,6621 (1990) and references cited therein.
  • 33.Schore N.E., Chem. Rev., 88, 1081 (1988).
  • 34.Leusink A.J., Budding H.A. and Marsman J.W.,.J. Organomet. Chem., 9, 285 (1967).
  • 35.Beckwith A.L.J., Hawthorne D.G. and Solomon D.H., Aust. J. Chem., 29, 995 (1976).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0002-0111
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