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Synthesis 2009(10): 1744-1752  
DOI: 10.1055/s-0028-1088075
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Diastereoselective Conjugate Addition-Elimination of Chiral Nickel(II) Glycinate with Activated Allylic Acetates for Asymmetric Synthesis of Glutamic Acid Derivatives

Jiang Wang, Jianmei Shi, Xiaodong Zhang, Daizong Lin, Hualiang Jiang, Hong Liu*
The Center for Drug Discovery and Design, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, P. R. of China
Fax: +86(21)50807088; e-Mail: hliu@mail.shcnc.ac.cn;
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Publication History

Received 13 March 2009
Publication Date:
27 April 2009 (online)

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Abstract

A practically feasible, diastereoselective conjugate addition-elimination reaction of a chiral nickel(II) complex of glycine 1 with allylic acetates 2 is described. The reaction pathway was successfully controlled, and the desired formation of a carbon-carbon bond was exclusively obtained with high diastereoselectivity. This reaction is an attractive route for the asymmetric synthesis of previously unavailable chainlike glutamic acid derivatives.

Key words

nickel(II) complex - asymmetric synthesis - glutamic acid - amino acids

    References

  • 1a Moloney MG. Nat. Prod. Rep.  1998,  15:  205 
    Search in Google Scholar
  • 1b Bräuner-Osborne H. Egebjerg J. Nielsen E. Madsen U. Krogsgaard-Larsen P. J. Med. Chem.  2000,  43:  2609 
    Search in Google Scholar
  • 1c Augelli-Szafran CE. Schwarz RD. Annu. Rep. Med. Chem.  2003,  38:  21 
    Search in Google Scholar
  • 2a Kotnik M. Humljan J. Contreras-Martel C. Oblak M. Kristan K. Hervé M. Blanot D. Urleb U. Gobec S. Dessen A. Solmajer T. J. Mol. Biol.  2007,  370:  107 
    Search in Google Scholar
  • 2b Baker SR. Bleakman D. Ezquerra J. Ballyk BA. Deverill M. Ho K. Kamboj RK. Collado I. Domíng C. Escribano A. Mateo AI. Pedregal C. Rubio A. Bioorg. Med. Chem. Lett.  2000,  10:  1807 
    Search in Google Scholar
  • 3a Pei P.-S. Meng Y.-C. Michael YC. Nein C.-C. Org. Lett.  2003,  5:  1761 
    Search in Google Scholar
  • 3b Hanessian S. Papeo G. Angiolini M. Fettis K. Beretta M. Munro A. J. Org. Chem.  2003,  68:  7204 
    Search in Google Scholar
  • Stereoselective synthesis of 3-substituted glutamic acid derivatives:
  • 4a Soloshonok VA. Curr. Org. Chem.  2007,  6:  341 ; as a review other representative examples:
    Search in Google Scholar
  • 4b Soloshonok VA. Cai C. Yamada T. Ueki H. Ohfune Y. Hruby VJ. J. Am. Chem. Soc.  2005,  127:  15296 
    Search in Google Scholar
  • 4c Herdeis C. Kelm B. Tetrahedron  2003,  59:  217 
    Search in Google Scholar
  • 4d Soloshonok VA. Cai C. Hruby VJ. Org. Lett.  2000,  2:  747 
    Search in Google Scholar
  • 4e Yamada T. Okada T. Sakaguchi K. Ohfune Y. Ueki H. Soloshonok VA. Org. Lett.  2006,  8:  5625 
    Search in Google Scholar
  • 5 Kobayashi S. Tsubogo T. Saito S. Yamashita Y. Org. Lett.  2008,  10:  807 
    CrossrefSearch in Google Scholar
  • 6 Ramachandran PV. Madhi S. Bland-Berry L. Reddy MVR. O’Donnell MJ. J. Am. Chem. Soc.  2005,  127:  13450 
    CrossrefPubMedSearch in Google Scholar
  • 7a Boyall D. Frantz DE. Carreira EM. Org. Lett.  2002,  4:  2605 
    Search in Google Scholar
  • 7b Sorochinsky A. Voloshin N. Markovsky A. Belik M. Yasuda N. Uekusa H. Ono T. Berbasov DO. Soloshonok VA. J. Org. Chem.  2003,  68:  7448 
    Search in Google Scholar
  • 7c Yasumoto M. Ueki H. Soloshonok VA. J. Fluorine Chem.  2007,  128:  736 
    Search in Google Scholar
  • 8a Cai C. Yamada T. Tiwari R. Hruby VJ. Soloshonok VA. Tetrahedron Lett.  2004,  45:  6855 
    Search in Google Scholar
  • 8b Belokon YN. Zel’tzer IE. Bakhmutov VI. Saporovaskaya MB. Ryzhov MG. Yanovsky AI. Struchkov YT. Belikov VM. J. Am. Chem. Soc.  1983,  105:  2010 
    Search in Google Scholar
  • 8c Belokon YN. Pure Appl. Chem.  1992,  64:  1917 
    Search in Google Scholar
  • 8d Belokon YN. Tararov VI. Maleev VI. Savel’eva TF. Ryzhov MG. Tetrahedron: Asymmetry  1998,  9:  4249 
    Search in Google Scholar
  • 9a Belokon YN. Bulychev AG. Vitt SV. Struchkov YT. Batsanov AS. Timofeeva TV. Tsyryapkin VA. Ryzhov MG. Lysova LA. Bakhmutov VI. Belikov VM. J. Am. Chem. Soc.  1985,  107:  4252 
    Search in Google Scholar
  • 9b Soloshonok VA. Kukhar VP. Galushko SV. Svistunova NY. Avilov DV. Kuzmina NA. Raevski NI. Struchkov YT. Pisarevsky AP. Belokon YN. J. Chem. Soc., Perkin Trans. 1  1993,  3143 
  • 9c Soloshonok VA. Avilov DV. Kukhar VP. Tetrahedron  1996,  52:  12433 
    Search in Google Scholar
  • 9d Belokon YN. Sagyan AS. Djamgaryan SA. Bakhmutov VI. Vitt SV. Batsanov AS. Struchkov YT. Belikov VM. J. Chem. Soc., Perkin Trans. 1  1990,  2301 
  • 9e Belokon YN. Sagyan AS. Djamgaryan SM. Bakhmutov VI. Belikov VM. Tetrahedron  1988,  44:  5507 
    Search in Google Scholar
  • 10a Soloshonok VA. Cai C. Hruby VJ. Angew. Chem. Int. Ed.  2000,  39:  2172 
    Search in Google Scholar
  • 10b Soloshonok VA. Cai C. Hruby VJ. Tetrahedron Lett.  2000,  41:  9645 
    Search in Google Scholar
  • 10c Cai C. Soloshonok VA. Hruby VJ. J. Org. Chem.  2001,  66:  1339 
    Search in Google Scholar
  • 10d Belokon YN. Bulychev AG. Pavlov VA. Fedorova EB. Tsyryapkin VA. Bakhmutov VA. Belikov VM. J. Chem. Soc., Perkin Trans. 1  1988,  2075 
  • 11a Gu X. Tang X. Cowell S. Ying J. Hruby VJ. Tetrahedron Lett.  2002,  43:  6669 
    Search in Google Scholar
  • 11b Taylor SM. Yamada T. Ueki H. Soloshonok VA. Tetrahedron Lett.  2004,  45:  9159 
    Search in Google Scholar
  • 11c Soloshonok VA. Tang X. Hruby VJ. Meervelt LV. Org. Lett.  2001,  3:  341 
    Search in Google Scholar
  • 11d Soloshonok VA. Boettiger TU. Bolene SB. Synthesis  2008,  2594 
  • 11e Belokon YN. Popkov AN. Saporovaskaya MB. Bakhmutov VI. Belikov VM. J. Chem. Soc., Chem. Commun.  1988,  1336 
  • 12 Jiang W. Ting S. Guang H.-D. Hua L.-J. Hong L. J. Org. Chem.  2008,  73:  8563 
    Search in Google Scholar