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Synthesis 2011(24): 3979-3990  
DOI: 10.1055/s-0031-1289584
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Combinatorial Approach towards a Library of Chiral γ-Lactams and 2,3-Disubstituted Pyrroles

Tobias Biletzki, Wolfgang Imhof*
Friedrich-Schiller-University Jena, Institute of Inorganic and Analytical Chemistry, Humboldtstraße 8, 07743 Jena, Germany
Fax: +49(3641)948102; e-Mail: Wolfgang.Imhof@uni-jena.de;
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Publikationsverlauf

Received 20 July 2011
Publikationsdatum:
03. November 2011 (online)

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Abstract

A library of heterocyclic products with a wide variety of organic residues is produced via a four-component reaction of α,β-unsaturated aldehydes, primary amines, carbon monoxide, and ethylene using a multi-reactor station with an array of 96 autoclaves employing the same high-pressure reaction conditions for all catalytic reactions. In the presence of Ru3(CO)12 as a precatalyst, mixtures of chiral γ-lactams and 2,3-disubstituted pyrroles are obtained. This combinatorial approach also enables us for the first time to set up rules relating to the effects of specific substituents in the substrates on the outcome of the respective catalytic reaction.

Key words

ruthenium - C-H activation - catalysis - γ-lactams - pyrroles

    References

  • 1 Dyker G. Angew. Chem. Int. Ed.  1999,  38:  1698 
    Suche in Google Scholar
  • 2 Guari Y. Sabo-Etienne S. Chaudret B. Eur. J. Inorg. Chem.  1999,  1047 
  • 3 Kakiuchi K. Murai S. Top. Organomet. Chem.  1999,  3:  47 
    Suche in Google Scholar
  • 4 Ritleng V. Sirlin C. Pfeffer M. Chem. Rev.  2002,  102:  1731 
    Suche in Google Scholar
  • 5 Chatani N. Chem. Rec.  2008,  8:  201 
    Suche in Google Scholar
  • 6 Ackermann L. Chem. Commun.  2010,  46:  4866 
    Suche in Google Scholar
  • 7 Kakiuchi F. Kochi T. Synthesis  2008,  3013 
  • 8 Kakiuchi F. Top. Organomet. Chem.  2007,  11:  1 
    Suche in Google Scholar
  • 9 Berger D. Imhof W. Chem. Commun.  1999,  1457 
  • 10 Berger D. Imhof W. Tetrahedron  2000,  56:  2015 
    Suche in Google Scholar
  • 11 Berger D. Göbel A. Imhof W. J. Mol. Catal. A: Chem.  2001,  165:  37 
    Suche in Google Scholar
  • 12 Imhof W. Berger D. Kötteritzsch M. Rost M. Schönecker B. Adv. Synth. Catal.  2001,  343:  795 
    Suche in Google Scholar
  • 13 Dönnecke D. Imhof W. Tetrahedron  2003,  59:  8499 
    Suche in Google Scholar
  • 14 Imhof W. Göbel A. J. Organomet. Chem.  2005,  690:  1092 
    Suche in Google Scholar
  • 15 Gillies G. Dönnecke D. Imhof W. Monatsh. Chem.  2007,  138:  683 
    Suche in Google Scholar
  • 16 Armat M. Canto M. Llor N. Escolano C. Molins E. Espinosa E. Bosch J. J. Org. Chem.  2002,  67:  5343 
    Suche in Google Scholar
  • 17 Thompson LA. inventors; U.S. Pat. Appl.  20020010172.  ; Chem. Abstr. 2002, 136, 118401
  • 18 Norrby SR. Drug Safety  1996,  15:  87 
    Suche in Google Scholar
  • 19 Horrobin DF. inventors; Eur. Pat. Appl.  37175.  ; Chem. Abstr. 1981, 96, 24802
  • 20 Herzog KJ, Jacobs R, Kang J, Simpson TR, and Woods JM. inventors; PCT Int. Appl. WO  2004080983.  ; Chem. Abstr. 2004, 141, 296296
  • 21 Elworthy TR. Brill ER. Chiou S.-S. Chu F. Harris JR. J. Med. Chem.  2004,  47:  6124 
    Suche in Google Scholar
  • 22 Xu X. Che X. Gao S. Wu J. Bai X. Synlett  2005,  1865 
  • 23 Frackenpohl J. Arvidsson PI. Schreiber JV. Seebach D. ChemBioChem  2001,  2:  445 
    Suche in Google Scholar
  • 24 Biletzki T. Stark A. Imhof W. Monatsh. Chem.  2010,  141:  413 
    Suche in Google Scholar
  • 25 Wasserscheid P. Weiss T. Agel F. Werth C. Jess A. Forster R. Angew. Chem. Int. Ed.  2007,  46:  7281 
    Suche in Google Scholar
  • 27 Hintermair U. Gutel T. Slawin AMZ. Cole-Hamilton DJ. Santini CC. Chauvin Y. J. Organomet. Chem.  2008,  693:  2407 
    Suche in Google Scholar
  • 28 Lecocq V. Santini CC. Chauvin Y. Basset J.-M. Galland J.-C. J. Mol. Catal. A: Chem.  2006,  246:  242 
    Suche in Google Scholar
  • 29 Park SB. Alper H. Chem. Commun.  2005,  1315 
  • 30 Anthony JL. Anderson JJ. Maginn EJ. Brennecke JF. J. Phys. Chem. B  2005,  109:  6366 
    Suche in Google Scholar
  • 31 Dudnik P. Tancrede JM. Rosenblum M. J. Organomet. Chem.  1969,  18:  365 
    Suche in Google Scholar
  • 32 Perrin DD. Armarego WLF. Perrin DR. Purification of Laboratory Chemicals   Pergamon Press; New York: 1980. 
26

Oxgaard, J.; Tang, Y.; Xu, Z.; Goddard, W. A.; Li, Z.; Cheng, J.; Chen, W. Conference Proceedings, AIChE Spring National Meeting, Houston, TX, USA, April 22-27, 2007; abstract p80644/1.