PDF herunterladen
Synlett 2011(4): 473-476  
DOI: 10.1055/s-0030-1259517
CLUSTER
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Pyrrolidine Sulfonamide Catalyzed Enantioselective Michael Addition of Cyclohexanones to Maleimides

Jian Wanga, Man-Man Zhangb, Shieli Zhanga, Zi-An Xub, Hao Lic, Xin-Hong Yu*b, Wei Wang*a,b,c
a Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA
Fax: +1(505)2772609; e-Mail: wwang@unm.edu;
b Department of Medicinal Chemistry, School of Pharmacy, East China University of Science & Technology, Shanghai 200237, P. R. of China
e-Mail: xhyu@ecust.edu.cn;
c Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Graduate School of the Chinese Academy of Sciences, Shanghai 201203, P. R. of China
Weitere Informationen

Publikationsverlauf

Received 20 November 2010
Publikationsdatum:
27. Januar 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

An organocatalytic enantioselective conjugate addition of cyclohexanones to maleimides has been developed. The process catalyzed by a (S)-pyrrolidine sulfonamide affords synthetically and medicinally useful chiral succinimides under mild reaction conditions.

Key words

cyclic ketones - maleimides - Michael reaction - pyrrolidine sulfonamide

    References and Notes

  • For biological studies on enantioenriched succinimides, see:
  • 1a Obrecht D. Abrecht C. Altorfer M. Bohdal U. Grieder A. Kleber M. Pfyffer P. Müller K. Helv. Chim. Acta  1996,  79:  1315 
    Google Scholar
  • 1b Ahmed S. Drug Des. Discovery  1996,  14:  77 
    Google Scholar
  • 1c Abell AD. Oldham MD. J. Org. Chem.  1997,  62:  1509 
    Google Scholar
  • 1d Curtin ML. Garland RB. Heyman HR. Frey RR. Michaelides MR. Li J. Pease LJ. Glaser KB. Marcotte PA. Davidsen SK. Bioorg. Med. Chem. Lett.  2002,  12:  2919 
    Google Scholar
  • 1e Barker DD. Lin H.-S. Carland JE. Chu CP.-Y. Chebib M. Brimble MA. Savage GP. McLeod MD. Bioorg. Med. Chem.  2005,  13:  4565 
    Google Scholar
  • 2a Brière J.-F. Charpentier P. Dupas G. Quèguiner G. Bourguignon J. Tetrahedron  1997,  53:  2075 
    Google Scholar
  • 2b Reddy PY. Kondo S. Toru T. Ueno Y. J. Org. Chem.  1997,  62:  2652 
    Google Scholar
  • 2c Katritzky AR. Yao J. Qi M. Chou Y. Sikora DJ. Davis S. Heterocycles  1998,  48:  2677 
    Google Scholar
  • 2d Ballini R. Bosica G. Cioci G. Fiorini D. Petrini M. Tetrahedron  2003,  59:  3603 
    Google Scholar
  • 2e Vo-Hoang Y. Gasse C. Vidal M. Garbay C. Galons H. Tetrahedron Lett.  2004,  45:  3603 
    Google Scholar
  • 2f de Figueiredo RM. Voith M. Fröhlich R. Christmann M. Synlett  2007,  391 
    Google Scholar
  • 2g Villa González S. Carlsen P. Eur. J. Org. Chem.  2007,  3495 
    Google Scholar
  • For selected examples, see:
  • 3a Corey EJ. Guzman-Perez A. Angew. Chem. Int. Ed.  1998,  37:  388 
    Google Scholar
  • 3b Christoffers J. Baro A. Angew. Chem. Int. Ed.  2003,  42:  1688 
    Google Scholar
  • 3c Shintani R. Ueyama K. Yamada I. Hayashi T. Org. Lett.  2004,  6:  3425 
    Google Scholar
  • 3d Alcaide B. Almendros P. Cabrero G. Ruiz MP. Org. Lett.  2005,  7:  3981 
    Google Scholar
  • 3e Shintani R. Duan W.-L. Hayashi T. J. Am. Chem. Soc.  2006,  128:  5628 
    Google Scholar
  • For selected reviews of organocatalysis, see:
  • 4a Berkessel A. Groger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis   Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 4b Dalko PI. Moisan L. Angew. Chem. Int. Ed.  2004,  43:  5138 
    Google Scholar
  • 4c Special issue on asymmetric organocatalysis: Acc. Chem. Res.  2004,  37:  487 
    Google Scholar
  • For recent reviews of organocatalytic conjugate addition reactions, see:
  • 4d Almasi D. Alonso DA. Najera C. Tetrahedron: Asymmetry  2007,  18:  299 
    Google Scholar
  • 4e Tsogoeva SB. Eur. J. Org. Chem.  2007,  1701 
    Google Scholar
  • 4f Marcelli T. van Maarseveen JH. Hiemstra H. Angew. Chem. Int. Ed.  2006,  45:  7496 
    Google Scholar
  • 4g Jarvo ER. Miller SJ. Tetrahedron  2002,  58:  2481 
    Google Scholar
  • 5 Bartoli G. Bosco M. Carlone A. Cavalli A. Locatelli M. Mazzanti A. Ricci P. Sambri L. Melchiorre P. Angew. Chem. Int. Ed.  2006,  45:  4966 
    CrossrefPubMedGoogle Scholar
  • 6a Li G.-Q. Li Y. Dai L.-X. You S.-L. Org. Lett.  2007,  9:  3919 
    Google Scholar
  • 6b Alcaide B. Almendros P. Cabrero GM. Ruiz P. Chem. Commun.  2008,  615 
    Google Scholar
  • For recent reviews of organocatalyzed conjugate addition reactions, see:
  • 7a Berner OM. Tedeschi L. Enders D. Eur. J. Org. Chem.  2002,  12:  1877 
    Google Scholar
  • 7b Taylor MS. Jacobsen EN. Angew. Chem. Int. Ed.  2006,  45:  1520 
    Google Scholar
  • 7c Almaºi D. Alonso DA. Nájera C. Tetrahedron: Asymmetry  2007,  18:  299 
    Google Scholar
  • 7d Tsogoeva SB. Eur. J. Org. Chem.  2007,  1701 
    Google Scholar
  • 7e Mukherjee S. Yang JW. Hoffmann S. List B. Chem. Rev.  2007,  107:  5471 
    Google Scholar
  • 7f Melchiorre P. Marigao M. Carlone A. Bartoli G. Angew. Chem. Int. Ed.  2008,  47:  6138 
    Google Scholar
  • 7g Bertelsen S. Jørgensen KA. Chem. Soc. Rev.  2009,  38:  2178 
    Google Scholar
  • 8a We reported the first example of organocatalytic enanioselective cascade Michael-aldol reaction involving maleimides: Zu L.-S. Xie H.-X. Li H. Wang J. Jiang W. Wang W. Adv. Synth. Catal.  2007,  349:  1882 
    Google Scholar
  • 8b Recently we also developed an organocatalytic Michael addtion of aldehydes to maleimides: Xue F. Liu L. Shilei Zhang S.-L. Duan W.-H. Wang W. Chem. Eur. J.  2010,  16:  7979 
    Google Scholar
  • Limited examples using maleimides in organocatalysis:
  • 9a Bartoli G. Bosco M. Carlone A. Cavalli A. Locatelli M. Mazzanti A. Ricci P. Sambri L. Melchiorre P. Angew. Chem. Int. Ed.  2006,  45:  4966 
    Google Scholar
  • 9b Zhao G. Xu Y. Sundén H. Eriksson L. Sayah M. Córdova A. Chem. Commun.  2007,  734 
    Google Scholar
  • 9c Ye W. Jiang Z. Zhao Y. Goh SLM. Leow D. Soh Y.-T. Tan C.-H. Adv. Synth. Catal.  2007,  349:  2454 
    Google Scholar
  • 9d Jiang Z. Ye W. Yang Y. Tan C.-H. Adv. Synth. Catal.  2008,  350:  2345 
    Google Scholar
  • 9e Jiang Z. Pan Y. Zhao Y. Ma T. Lee R. Yang Y. Huang K.-W. Wong MW. Tan C.-H. Angew. Chem. Int. Ed.  2009,  48:  3627 
    Google Scholar
  • Barbas and co-workers reported the Michael addition of acetone to maleimide without asymmetric induction:
  • 10a Tanaka F. Thayumanavan R. Barbas CF. J. Am. Chem. Soc.  2003,  125:  8523 
    Google Scholar
  • 10b Tanaka F. Thayumanavan R. Mase N. Barbas CF. Tetrahedron Lett.  2004,  45:  325 
    Google Scholar
  • 10c During our investiagtion, Liang, Ye, and co-workers disclosed a nice Michael addition of ketones to maleimides catalyzed by a chiral primary amine: Yu F. Sun X. Jin Z. Wen S. Liang X. Ye J. Chem. Commun.  2010,  4589 
    Google Scholar
  • For examples of reactions promoted by (S)-pyrrolidine sulfonamide, see:
  • 11a Wang W. Wang J. Li H. Tetrahedron Lett.  2004,  45:  7235 
    Google Scholar
  • 11b Wang W. Wang J. Li H. Tetrahedron Lett.  2004,  45:  7243 
    Google Scholar
  • 11c Wang W. Li H. Wang J. Tetrahedron Lett.  2004,  45:  8229 
    Google Scholar
  • 11d Wang W. Wang J. Li H. Angew. Chem. Int. Ed.  2005,  44:  1369 
    Google Scholar
  • 11e Wang W. Li H. Wang J. Tetrahedron Lett.  2005,  46:  5077 
    Google Scholar
  • 11f Wang J. Li H. Mei Y. Lou B. Xu D. Xie D. Guo H. Wang W. J. Org. Chem.  2005,  70:  5678 
    Google Scholar
  • 11g Wang J. Li H. Lou B. Zu L. Guo H. Wang W. Chem. Eur. J.  2006,  12:  4321 
    Google Scholar
  • 11h Wang J. Li H. Zu L.-S. Wang W. Adv. Synth. Catal.  2006,  348:  425 
    Google Scholar
  • 11i Zu L.-S. Wang J. Li H. Yu X.-H. Wang W. Org. Lett.  2006,  8:  3077 
    Google Scholar
  • 11j Cao C.-L. Sun X.-L. Zhou J.-L. Tang Y. J. Org. Chem.  2007,  72:  4073 
    Google Scholar
  • 11k Cao C.-L. Sun X.-L. Kang Y.-B. Tang Y. Org. Lett.  2007,  9:  4151 
    Google Scholar
  • Examples of other sulfonamide-catalyzed reactions:
  • 11l Ishihara K. Kosugi Y. Akakur M. J. Am. Chem. Soc.  2004,  126:  12212 
    Google Scholar
  • 11m Kano T. Yamaguchi Y. Tokuda O. Maruoka K. J. Am. Chem. Soc.  2005,  127:  16408 
    Google Scholar
  • For a review of l-proline-catalyzed reactions, see:
  • 12a List B. Tetrahedron  2002,  58:  5573 
    Google Scholar
  • 12b Movassaghi M. Jacobsen EN. Science  2002,  298:  1904 
    Google Scholar
  • For examples of l-prolinamide-promoted reaction, see:
  • 13a Wang W. Wang J. Li H. Org. Lett.  2004,  6:  2817 
    Google Scholar
  • 13b Chen J.-R. Lu H.-H. Li X.-Y. Cheng L. Wan J. Xiao W.-J. Org. Lett.  2005,  7:  4543 
    Google Scholar
  • 13c Dodda R. Zhao C.-G. Org. Lett.  2006,  8:  4911 
    Google Scholar
  • 13d Aratake S. Itoh T. Okano T. Usui T. Shoji M. Hayashi Y. Chem. Commun.  2007,  2524 
    Google Scholar
  • 13e Peng Y.-Y. Liu H. Cui M. Cheng J.-P. Chin. J. Chem.  2007,  25:  962 
    Google Scholar
  • 14 For a review of reactions catalyzed by chiral pyrrolidine diamine derivatives, see: Notz W. Tanaka F. Barbas CF. Acc. Chem. Res.  2004,  37:  580 
    CrossrefPubMedGoogle Scholar
  • 15 For a reivew of MacMillan’s imidazolindinone-catalyzed reactions (iminium catalysis), see: Lelais G. MacMillan DWC. Aldrichimica Acta  2006,  39:  79 
    Google Scholar
  • Reviews of chiral diarylprolinol silyl ether catalyzed reactions, see:
  • 16a Enders D. Grondal C. Huttl MRM. Angew. Chem. Int. Ed.  2007,  46:  1570 
    Google Scholar
  • 16b Palomo C. Mielgo A. Angew. Chem. Int. Ed.  2006,  45:  7876 
    Google Scholar
17

CCDC-664491 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk.