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Synthesis 2002(3): 0375-0380
DOI: 10.1055/s-2002-20039
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-(Dialkylaminoalkyl)alcohols by Homogeneously Catalyzed Hydrogenolysis of Cyclic N,O-Acetals

Vitali I. Tararov*a, Renat Kadyrovb, Thomas H. Riermeierb, Armin Börner*a
a Institut für Organische Katalyseforschung an der Universität Rostock e.V., Buchbinderstr. 5/6, 18055 Rostock, Germany
Fax: +49(381)4669324; e-Mail: vitali.tararov@ifok.uni-rostock.de; e-Mail: armin.boerner@ifok.uni-rostock.de;
b Degussa AG, Projekthaus Katalyse, Geschäftsbereich Creavis, Industriepark Hoechst, Gebäude G 830, 65926 Frankfurt/Main, Germany
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Publikationsverlauf

Received 6 November 2001
Publikationsdatum:
28. Juli 2004 (online)

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Abstract

The homogeneously catalyzed hydrogenation of 1,3-oxazolidines affording unsymmetrically substituted 2-N-(dialkylamino)ethanols is reported showing for the first time that Rh(I) catalysts based on chelating diphosphines can be advantageous for this reaction.

Key words

hydrogenation - transition metals - catalysis - amino alcohols

    References

  • 1a Alberola A. Alvarez MA. Andres C. Gonzalez A. Pedros R. Synthesis  1990,  156 
    Thieme Connect
  • 1b Page PCB. Heaney H. Rassias GA. Reignier S. Sampler EP. Talib S. Synlett  2000,  104 ; and references cited therein
    Thieme Connect
  • 2 Azzena U. Melloni G. Nigra C. J. Org. Chem.  1993,  58:  6707 
    Suche in Google Scholar
  • 3 Pohland A. Sullivan HR. McMahon RE. J. Am. Chem. Soc.  1957,  66:  1442 
    Suche in Google Scholar
  • 1,3-Oxazolidine:
  • 5a Raßhofer W. In Houben-Weyl, Methoden der Organischen Chemie   Band E14a/2:  Hagemann H. Klamann D. Thieme; Stuttgart: 1991.  p.595 
    Suche in Google Scholar
  • 5b Raßhofer W. In Houben-Weyl, Methoden der Organischen Chemie   Band E14a/2:  Hagemann H. Klamann D. Thieme; Stuttgart: 1991.  p.679 
    Suche in Google Scholar
  • 6 Padva A. Dent W. J. Org. Chem.  1987,  52:  235 
    CrossrefSuche in Google Scholar
  • 7 Ulbricht TLV. Vester F. Tetrahedron  1962,  18:  629 
    CrossrefSuche in Google Scholar
  • 8 Bergmann ED. Zimkin E. Pinchas P. Recl. Trav. Chim. Pays-Bas  1952,  71:  237 
    Suche in Google Scholar
  • 9 Kon GAR. Roberts JJ. J. Chem. Soc.  1950,  978 
  • 10 Neelakantan L. J. Org. Chem.  1971,  36:  225 
    Suche in Google Scholar
  • 11 Itsuno S. Ito K. Hirao A. Nakahama S. J. Chem. Soc., Perkin Trans. 1  1984,  2887 
    Crossref
  • 12 Sung DWL. Hodge P. Stratford PW. J. Chem. Soc., Perkin Trans. 1  1999,  1463 
    Crossref
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Tararov, V. I.; Kadyrov, R.; Riermeier, T. H.;, Börner, A. Adv. Synth. Catal., in press.