Synlett 2021(4): 462-463  
DOI: 10.1055/s-0030-1259544
CLUSTER
© Georg Thieme Verlag Stuttgart ˙ New York

Cluster Preface: Challenges of Proline-Based Aminocatalysis

Benjamin List*
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Fax: +49(208)3062982; e-Mail: list@mpi-muelheim.mpg.de;
Further Information

Publication History

Received 12 January 2011
Publication Date:
16 February 2011 (online)

Abstract

During the last eleven years, aminocatalysis, the catalysis of carbonyl transformations via iminium ion and enamine intermediates has become a highly successful and general approach to asymmetric synthesis. There are now several dozens of different ­reaction types with hundreds of variants that are mediated by primary and secondary amine catalysts, of which proline continues to be a privileged motif. This Cluster highlights recent attempts towards solving some of the remaining challenges in the area.

    References and Notes

  • 1 List B. Lerner RA. Barbas III CF. J. Am. Chem. Soc.  2000,  122:  2395 
  • 2For a review on enamine catalysis, see:
  • 2 Mukherjee S. Yang JW. Hoffmann S. List B. Chem. Rev.  2007,  107:  5471 
  • 3 Ahrendt KA. Borths CJ. MacMillan DWC. J. Am. Chem. Soc.  2000,  122:  4243 
  • For other selected reviews covering aminocatalysis see:
  • 4a List B. Synlett  2001,  1675 
  • 4b List B. Acc. Chem. Res.  2004,  37:  548 
  • 4c List B. Chem. Commun.  2006,  819 
  • 4d Lelais G. MacMillan DWC. Aldrichimica Acta  2006,  39:  79 
  • 4e List B. Yang JW. Science  2006,  313(5793):  1584 
  • 4f Erkkilä A. Majander I. Pihko PM. Chem. Rev.  2007,  107:  5416 
  • 4g Enders D. Grondal C. Huettl MRM. Angew. Chem. Int. Ed.  2007,  46:  1570 
  • 4h MacMillan DWC. Nature  2008,  455:  304 
  • 4i Enders D. Narine AA. J. Org. Chem.  2008,  73:  7857 
  • 4j Kano T. Maruoka K. Chem. Commun.  2008,  43:  5465 
  • 4k Bertelsen S. Jørgensen KA. Chem. Soc. Rev.  2009,  38:  2178 
  • 4l Pihko PM. Majander I. Erkkilä A. Top. Curr. Chem.  2010,  291:  29 
  • 4m Brazier JB. Tomkinson NCO. Top. Curr. Chem.  2010,  291:  281 
  • 4n List B. Angew. Chem. Int. Ed.  2010,  49:  1730 
  • 5a

    see ref. 1

  • 5b Northrup AB. MacMillan DWC. J. Am. Chem. Soc.  2002,  124:  6798 
  • 5c List B. J. Am. Chem. Soc.  2000,  122:  9336 
  • 5d Yang JW. Stadler M. List B. Angew. Chem. Int. Ed.  2007,  46:  609 
  • 5e Yang JW. Chandler C. Stadler M. Kampen D. List B. Nature  2008,  452:  453 
  • 5f Chi Y. Gellman SH. Org. Lett.  2005,  7:  4253 
  • 5g List B. J. Am. Chem. Soc.  2002,  124:  5656 
  • 5h Bøgevig A. Juhl K. Kumaragurubaran N. Zhuang W. Jørgensen KA. Angew. Chem. Int. Ed.  2002,  41:  1790 
  • 5i Zhong G. Angew. Chem. Int. Ed.  2003,  42:  4247 
  • 5j Brown SP. Brochu MP. Sinz CJ. MacMillan DWC. J. Am. Chem. Soc.  2003,  125:  10808 
  • 5k Hayashi Y. Yamaguchi J. Hibino K. Shoji M. Tetrahedron Lett.  2003,  44:  8293 
  • 5l Franzén J. Marigo M. Fielenbach D. Wabnitz TC. Kjærsgaard A. Jørgensen KA. J. Am. Chem. Soc.  2005,  127:  18296