Download PDF
Synthesis 2009(22): 3744-3750  
DOI: 10.1055/s-0029-1217013
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Merrifield Resin Supported Ionic Liquids/l-Proline as Efficient and Recyclable Catalyst Systems for Asymmetric Aldol Reaction

Zuli Wanga, Jincan Yana, Xiuli Zhang*b,c, Lei Wang*a,c
a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
b College of Science, Anhui Agricultural University, Hefei, Anhui 230036, P. R. of China
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;
Further Information

Publication History

Received 3 June 2009
Publication Date:
23 September 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Merrifield resin supported ionic liquids/l-proline as efficient and recyclable catalyst systems for asymmetric aldol reaction have been developed. l-Proline with Merrifield resin supported ionic liquids can catalyze asymmetric aldol reaction smoothly and generate the corresponding products in good to excellent yields and ee values. In addition, the supported catalyst systems can be recycled simply by filtration and reused for five times without significant decrease in activity.

Key words

Merrifield resin - organocatalyst - aldol reaction - l-proline - ionic liquids - supported catalysts

    References

  • 1a Heathcock CH. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991.  Chap. 1.5.
    Google Scholar
  • 1b Heathcock CH. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991.  Chap. 1.6.
    Google Scholar
  • 1c Kim BM. Williams SF. Masamune S. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991.  Chap. 1.7.
    Google Scholar
  • 2a Mukaiyama T. Tetrahedron  1999,  55:  8609 
    Google Scholar
  • 2b Nicolaou KC. Vourloumis D. Wissinger N. Baran PS. Angew. Chem. Int. Ed.  2000,  39:  44 
    Google Scholar
  • 2c Evans DA. Ratz AM. Huff BE. Sheppard GS. J. Am. Chem. Soc.  1995,  117:  3448 
    Google Scholar
  • 2d Narasaka K. Pai FC. Tetrahedron  1984,  40:  2233 
    Google Scholar
  • 2e Keck GE. Wager CA. Sell T. Wager TT. J. Org. Chem.  1999,  64:  2172 
    Google Scholar
  • For examples, see:
  • 3a Barbas CF. Heine A. Zhong G. Hoffmann T. Gramatikova S. Björnestedt R. List B. Anderson J. Stura EA. Wilson IA. Lerner RA. Science  1997,  278:  2085 
    Google Scholar
  • 3b Hoffmann T. Zhong G. List B. Shabat D. Anderson J. Gramatikova S. Lerner RA. Barbas CF. J. Am. Chem. Soc.  1998,  120:  2768 
    Google Scholar
  • 3c List B. Shabat D. Barbas CF. Lerner RA. Chem. Eur. J.  1998,  4:  881 
    Google Scholar
  • 4a Yamada YMA. Yoshikawa N. Sasai H. Shibasaki M. Angew. Chem., Int. Ed.  1997,  36:  1871 
    Google Scholar
  • 4b Yoshikawa N. Yamada YMA. Das J. Sasai H. Shibasaki M. J. Am. Chem. Soc.  1999,  121:  4168 
    Google Scholar
  • 5a Hartikka A. Arvidsson PI. Tetrahedron: Asymmetry  2004,  15:  1831 
    Google Scholar
  • 5b Torii H. Nakadai M. Ishihara K. Saito S. Yamamoto H. Angew. Chem. Int. Ed.  2004,  43:  1983 
    Google Scholar
  • 5c For a review, see: Saito S. Yamamoto H. Acc. Chem. Res.  2004,  37:  570 
    Google Scholar
  • For recent reviews, see:
  • 6a Silvestri MG. Desantis G. Mitchell M. Wong C.-H. Top. Stereochem.  2003,  23:  267 
    Google Scholar
  • 6b Sukumaran J. Hanefeld U. Chem. Soc. Rev.  2005,  34:  530 
    Google Scholar
  • 6c Samland AK. Sprenger GA. Appl. Microbiol. Biotechnol.  2006,  71:  253 
    Google Scholar
  • 7a Reymond J.-L. J. Mol. Catal. B: Enzym.  1998,  5:  331 
    Google Scholar
  • 7b Zhu X. Tanaka F. Hu Y. Heine A. Fuller R. Zhong G. Olson AJ. Lerner RA. Barbas CF. Wilson IA. J. Mol. Biol.  2004,  343:  1269 
    Google Scholar
  • 8 Movassaghi M. Jacobsen EN. Science  2002,  298:  1904 
    CrossrefPubMedGoogle Scholar
  • 9a Eder U. Sauer G. Wiechert R. Angew. Chem., Int. Ed. Engl.  1971,  10:  496 
    Google Scholar
  • 9b Hajos ZG. Parrish DR. J. Org. Chem.  1974,  39:  1615 
    Google Scholar
  • 10a List B. Lerner RA. Barbas CF. J. Am. Chem. Soc.  2000,  122:  2395 
    Google Scholar
  • 10b Sakthivel K. Notz W. Bui T. Barbas CF. J. Am. Chem. Soc.  2001,  123:  5260 
    Google Scholar
  • 11 Cordova A. Zou W. Dziedzic P. Ibrahem I. Reyes E. Xu Y. Chem. Eur. J.  2006,  12:  5383 
    CrossrefGoogle Scholar
  • 12 List B. Chem. Commun.  2006,  819 
    CrossrefGoogle Scholar
  • 13 Miao W. Chan T.-H. Adv. Synth. Catal.  2006,  348:  1711 
    CrossrefGoogle Scholar
  • 14 Gruttadauria M. Giacalone F. Eur. J. Org. Chem.  2007,  4688 
    CrossrefGoogle Scholar
  • 15 Yan J. Wang L. Synthesis  2008,  2065 
    Article in Thieme ConnectGoogle Scholar
  • 16 Fernandez-Lopez R. Kofoed J. Machuqueiro M. Darbre T. Eur. J. Org. Chem.  2005,  5268 
    CrossrefGoogle Scholar
  • 17 Chandrasekhar S. Reddy NR. Sultana SS. Narsihmulu C. Reddy KV. Tetrahedron  2006,  62:  338 
    CrossrefGoogle Scholar
  • 18 Zhou Y. Shan Z. Tetrahedron: Asymmetry  2006,  17:  1671 
    CrossrefGoogle Scholar
  • 19 Zhou L. Wang L. Chem. Lett.  2007,  36:  628 
    CrossrefGoogle Scholar
  • 20 Choudary BM. Chakrapani L. Ramani T. Kumar KV. Kantam ML. Tetrahedron  2006,  62:  9571 
    CrossrefGoogle Scholar
  • 21 Chen J.-R. An X.-L. Zhu X.-Y. Wang X.-F. Xiao W.-J. J. Org. Chem.  2008,  74:  6006 
    Google Scholar
  • 22 Lei M. Shi L.-X. Li G. Chen S.-L. Fang W.-H. Ge Z.-M. Cheng T.-M. Li R.-T. Tetrahedron  2007,  63:  7892 
    CrossrefGoogle Scholar
  • 23 Gu Q. Wang X.-F. Wang L. Wu X.-Y. Zhou Q.-L. Tetrahedron: Asymmetry  2006,  17:  1537 
    CrossrefGoogle Scholar