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Synthesis 2004(12): 2047-2051  
DOI: 10.1055/s-2004-829183
PAPER
© Georg Thieme Verlag Stuttgart · New York

Versatile Synthesis of Chiral Aminophosphine Phosphinites (AMPPs) as Ligands for Enantioselective Hydrogenation

Natalia V. Dubrovinaa, Vitali I. Tararova, Zenfira Kadyrovaa, Axel Monseesb, Armin Börner*a,c
a Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V., Buchbinderstr. 5/6, 18055 Rostock, Germany
b Degussa AG, Projekthaus Katalyse, Industriepark Hoechst, Gebäude G 830, 65926 Frankfurt/Main, Germany
c Fachbereich Chemie der Universität Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4669324; e-Mail: armin.boerner@ifok.uni-rostock.de;
Further Information

Publication History

Received 3 May 2004
Publication Date:
27 July 2004 (online)

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Abstract

New chiral aminophosphine phosphinite (AMPP) ligands with different P-aryl substituents were prepared from (1R,3S,4S)-2-azabicyclo[2.2.1]hept-3-ylmethanol by a new and chemoselective synthetic approach. The ligands showed good enantioselectivity (up to 91%) in the Rh-catalyzed enantioselective hydrogenation of benchmark substrates.

Key words

hydrogenation - transition metals - asymmetric catalysis - amino alcohols - phosphorus

    References

  • 1a Ohkuma T. Kitamura M. Noyori R. Asymmetric Hydrogenation, In Catalytic Asymmetric Synthesis   Ojima I. Wiley-VCH; New York: 2000.  p.1 
  • 1b Asymmetric Catalysis on Industrial Scale   Blaser HU. Schmidt E. Wiley-VCH; Weinheim: 2003. 
  • 2 Petit M. Mortreux A. Petit F. Buono G. Pfeiffer G. New. J. Chem.  1983,  7:  593 
    Search in Google Scholar
  • 3a Brunner H. Zettlmeier W. Handbook of Enantioselective Catalysis with Transition Metal Compounds, Ligands   Vol. 2:  VCH; Weinheim: 1993. 
    Search in Google Scholar
  • 3b Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis   Wiley; New York: 1995. 
  • 4 For a recent review, see: Agbossou-Niedercorn F. Suisse I. Coord. Chem. Rev.  2003,  242:  145 ; and references cited therein
    CrossrefSearch in Google Scholar
  • 5 Jugé S. Stephan M. Merdés R. Genêt J.-P. Halut-Desportes S. J. Chem. Soc., Chem. Commun.  1993,  531 
    Crossref
  • 6 Kosolapoff GM. Maier L. Organic Phosphorus Compounds   Vol. 4:  Wiley; New York: 1972.  p.504 
    Search in Google Scholar
  • 8 Coppola GM. Schuster HF. Asymmmetric Synthesis: Construction of Chiral Molecules using Amino Acids   Wiley Interscience; New York: 1987. 
  • 9a Brandt P. Andersson PG. Synlett  2000,  1092 ; and references cited therein
    Thieme Connect
  • 9b Genov M. Scherer G. Studer M. Pfalz A. Synthesis  2002,  2037 
    Thieme Connect
  • 10a Tararov VI. Kadyrov R. Kadyrova Z. Dubrovina N. Börner A. Tetrahedron: Asymmetry  2002,  13:  25 
    CrossrefSearch in Google Scholar
  • 10b Ekegren JK. Modin SA. Alonso DA. Andersson PG. Tetrahedron: Asymmetry  2002,  13:  447 
    CrossrefSearch in Google Scholar
  • 11 Cesarotti E. Chiesa A. Ciani G. Sironi A. J. Organomet. Chem.  1983,  251:  79 
    CrossrefSearch in Google Scholar
  • 12 McEwen WE. Janes AB. Knapczyk JW. Kyllingstad VL. Shiau W.-I. Shore S. Smith JH. J. Am. Chem. Soc.  1978,  100:  7304 
    CrossrefSearch in Google Scholar
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This work is part of the Ph.D. thesis of Dubrovina, N. V.; Rostock, 2003.