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Synlett 2012(5): 765-767  
DOI: 10.1055/s-0031-1290598
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Investigation of Additive Effects in Enantioselective Copper-Catalysed C-H Insertion and Aromatic Addition Reactions of α-Diazocarbonyl Compounds

Catherine N. Slatterya, Leslie-Ann Clarkea, Shane O’Neilla, Aoife Ringa, Alan Forda, Anita R. Maguire*b
a Department of Chemistry and Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
b Department of Chemistry, School of Pharmacy and Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland
Fax: +353(21)4274097; e-Mail: a.maguire@ucc.ie;
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Publikationsverlauf

Received 4 November 2011
Publikationsdatum:
28. Februar 2012 (online)

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Abstract

Significant enhancements in enantioselectivities and reaction efficiencies in asymmetric copper-catalysed C-H insertion and aromatic addition reactions of α-diazocarbonyl compounds in the presence of various group I salts are reported. For the first time in carbenoid chemistry, evidence for the critical role of the metal cation is described.

Key words

diazocarbonyl - copper catalysis - C-H insertion - ­Buchner reaction - bis(oxazoline) ligands

    References and Notes

  • 1 Slattery CN. Ford A. Maguire AR. Tetrahedron  2010,  66:  6681 
    Google Scholar
  • 2 Doyle MP. McKervey MA. Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   Wiley-Interscience; New York: 1998. 
    Google Scholar
  • 3 Doyle MP. Duffy R. Ratnikov M. Zhou L. Chem. Rev.  2010,  110:  704 
    Google Scholar
  • 4 Davies HML. Beckwith REJ. Chem. Rev.  2003,  103:  2861 
    Google Scholar
  • 5 Flynn CJ. Elcoate CJ. Lawrence SE. Maguire AR. J. Am. Chem. Soc.  2010,  132:  1184 
    Google Scholar
  • 6 Fraile JM. Garcia JI. Mayoral JA. Roldan M. Org. Lett.  2007,  9:  731 
    Google Scholar
  • 7 Slattery CN. Maguire AR. Org. Biomol. Chem.  2011,  9:  667 
    Google Scholar
  • 8 O’Neill S. O’Keeffe S. Harrington F. Maguire AR. Synlett  2009,  2312 
    Google Scholar
  • 9 O’Keeffe S. Harrington F. Maguire AR. Synlett  2007,  2367 
    Google Scholar
  • 10 Liu B. Zhu S.-F. Zhang W. Chen C. Zhou Q.-L. J. Am. Chem. Soc.  2007,  129:  5834 
    Google Scholar
  • 11 Chen C. Zhu S.-F. Liu B. Wang L.-X. Zhou Q.-L. J. Am. Chem. Soc.  2007,  129:  12616 
    Google Scholar
  • 12 Krossing I. Raabe I. Angew. Chem. Int. Ed.  2004,  43:  2066 
    Google Scholar
  • 13 Zhu S.-F. Xie J.-B. Zhang Y.-Z. Li S. Zhou Q.-L. J. Am. Chem. Soc.  2006,  128:  12886 
    Google Scholar
  • 14 Rosenberg ML. Vlašaná K. Gupta NS. Wragg D. Tilset M. J. Org. Chem.  2011,  76:  2465 
    Google Scholar
  • 15 Krumper JR. Gerisch M. Suh JM. Bergman RG. Tilley TD. J. Org. Chem.  2003,  68:  9705 
    Google Scholar
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Presence of NaCl confirmed by PXRD analysis (see Supporting Information for details).