Synlett 2012(1): 1-5  
DOI: 10.1055/s-0031-1290111
SYNPACTS
© Georg Thieme Verlag Stuttgart ˙ New York

Recent Developments in Asymmetric Coupling of Enolates

Jianrong (Steve) Zhou*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Fax: +(65)67911961; e-Mail: jrzhou@ntu.edu.sg;
Further Information

Publication History

Received 29 October 2011
Publication Date:
13 December 2011 (online)

Abstract

Recent progress in transition-metal-catalyzed, asymmetric couplings of carbonyl compounds is summarized. Particular emphasis is placed on the intermolecular processes that form tertiary stereocenters, which was a challenging problem for many years.

    References

  • 1 Semmelhack MF. Stauffer RD. Rogerson TD. Tetrahedron Lett.  1973,  14:  4519 
  • 2a Palucki M. Buchwald SL. J. Am. Chem. Soc.  1997,  119:  11108 
  • 2b Hamann BC. Hartwig JF. J. Am. Chem. Soc.  1997,  119:  12382 
  • 2c Satoh T. Kawamura Y. Miura M. Nomura M. Angew. Chem. Int. Ed.  1997,  36:  1740 
  • 3 Landoni MF. Soraci A. Curr. Drug Metab.  2001,  2 37 
  • 4 Harrington PJ. Lodewijk E. Org. Process Res. Dev.  1997,  1:  72 
  • Reviews:
  • 5a Bellina F. Rossi R. Chem. Rev.  2010,  110:  1082 
  • 5b Johansson CCC. Colacot TJ. Angew. Chem. Int. Ed.  2010,  49:  676 
  • 5c Burtoloso ACB. Synlett  2009,  320 
  • 6 Huang Z. Liu Z. Zhou J. J. Am. Chem. Soc.  2011,  133:  15882 
  • 7 Allen AE. MacMillan DWC. J. Am. Chem. Soc.  2011,  133:  4260 
  • 8 Harvey JS. Simonovich SP. Jamison CR. MacMillan DWC. J. Am. Chem. Soc.  2011,  133:  13782 
  • 9 Bigot A. Williamson AE. Gaunt MJ. J. Am. Chem. Soc.  2011,  133:  13778 
  • 10 A review on Ni-catalyzed, asymmetric couplings of α-halocarbonyl compounds: Glorius F. Angew. Chem. Int. Ed.  2008,  47:  8347 
  • 11a Liao X. Weng Z. Hartwig JF. J. Am. Chem. Soc.  2008,  130:  195 
  • 11b Hamada T. Chieffi A. Åhman J. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  1261 
  • 11c Ge S. Hartwig JF. J. Am. Chem. Soc.  2011,  133:  16330 
  • 12 Spielvogel DJ. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  3500 
  • Examples of arylations of amides:
  • 13a Taylor AM. Altman RA. Buchwald SL. J. Am. Chem. Soc.  2009,  131:  9900 
  • 13b Lee S. Hartwig JF. J. Org. Chem.  2001,  66:  3402 
  • 14 García-Fortanet J. Buchwald SL. Angew. Chem. Int. Ed.  2008,  47:  8108 
  • 15 Asymmetric coupling of aryl bromides and one silyl ketene acetal was reported to give moderate ee: Galarini R. Musco A. Pontellini R. Santi R. J. Mol. Catal.  1992,  72:  L11 
  • 16 Liu X. Hartwig JF. : J. Am. Chem. Soc.  2004,  126:  5182 
  • 17 Carfagna C. Musco A. Sallese G. Santi R. Fiorani T.
    J. Org. Chem.  1991,  56:  261 
  • 18 Copper-catalyzed enantioselective arylation of 2-methyl acetoacetates: Xie X. Chen Y. Ma D. J. Am. Chem. Soc.  2006,  128:  16050 
  • Intramolecular, asymmetric arylation of aldehydes:
  • 19a Um JM. Gutierrez O. Schoenebeck F. Houk KN. MacMillan DWC. J. Am. Chem. Soc.  2010,  132:  6001 
  • 19b Conrad JC. Kong J. Laforteza BN. MacMillan DWC. J. Am. Chem. Soc.  2009,  131:  11640