Download PDF
Synthesis 2012; 44(16): 2601-2606
DOI: 10.1055/s-0032-1316577
paper
© Georg Thieme Verlag Stuttgart · New York

Secondary-Amine-Catalyzed Asymmetric Michael Addition of N-tert-Butoxycarbonyl-Protected Oxindoles to Maleimides

Xuena Yang
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: enders@rwth-aachen.de
,
Chuan Wang
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: enders@rwth-aachen.de
,
Qijian Ni
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: enders@rwth-aachen.de
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Fax: +49(241)8092127   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 24 May 2012

Accepted: 31 May 2012

Publication Date:
06 July 2012 (online)

    Permissions and Reprints All articles of this category


Abstract

A secondary-amine-catalyzed asymmetric Michael addition of 3-substituted N-(tert-butoxycarbonyl)oxindoles to maleimides with activation by a Brønsted base gives the corresponding products in high yields (86–98%), excellent diastereomeric ratios (dr > 99:1), and high enantiomeric excesses (86–91% ee).

Key words

Brønsted base - Michael addition - heterocycles - organo­catalysis - oxindole

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

    • 1a Mehta RG, Liu J, Constantinou A, Hawthorne M, Pezzuto JM, Moon RC, Moriarty RM. Anticancer Res. 1994; 14: 1209
    • 1b Tokunaga T, Hume WE, Umezome T, Okazaki K, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, Nagata R. J. Med. Chem. 2001; 44: 4641
      CrossrefPubMed
    • 1c Hewawasam P, Erway M, Moon SL, Knipe J, Weiner H, Boissard CG, Post-Munson DJ, Gao Q, Huang S, Gribkoff VK, Meanwell NA. J. Med. Chem. 2002; 45: 1487
      CrossrefPubMed
    • 1d Hewawasam P, Gribkoff VK, Pendri Y, Dworetzky SI, Meanwell NA, Martinez E, Boissard CG, Post-Munson DJ, Trojnacki JT, Yeleswaram K, Pajor LM, Knipe J, Gao Q, Perrone R, Starrett JE. Jr. Bioorg. Med. Chem. Lett. 2002; 12: 1023
      Crossref
    • 1e Dandia A, Sati M, Arya K, Sharma R, Loupy A. Chem. Pharm. Bull. 2003; 51: 1137
      CrossrefPubMed
    • 1f Serradeil-Le Gal C, Derick S, Brossard G, Manning M, Simiand J, Gaillard R, Griebel G, Guillon G. Stress 2003; 6: 199
      Crossref
    • 1g Neel DA, Brown ML, Lander PA, Grese TA, Defauw JM, Doti RA, Fields T, Kelly SA, Smith S, Zimmerman KM, Steinberg MI, Jadhav PK. Bioorg. Med. Chem. Lett. 2005; 15: 2553
      Crossref
    • 1h Bernard K, Bogliolo S, Ehrenfeld J. Br. J. Pharmacol. 2005; 144: 1037
      CrossrefPubMed
    • 1i Luk K.-C, So S.-S, Zhang J, Zhang Z. WO 2006136606, 2006
    • 1j Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stuckey J, Krajewski K, Roller PP, Wang S. J. Med. Chem. 2006; 49: 3432
      CrossrefPubMed
    • 1k Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Wu TY.-H, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2105
      Crossref
    • 1l Pedras MS. C, Hossain M. Org. Biomol. Chem. 2006; 4: 2581
      CrossrefPubMed
    • 1m Uddin MK, Reignier SG, Coulter T, Montalbetti C, Grånäs C, Butcher S, Krog-Jensen C, Felding J. Bioorg. Med. Chem. Lett. 2007; 17: 2854
      Crossref
    • 2a Kawasaki T, Ogawa A, Takashima Y, Sakamoto M. Tetrahedron Lett. 2003; 44: 1591
      Crossref
    • 2b Huang A, Kodanko JJ, Overman LE. J. Am. Chem. Soc. 2004; 126: 14043
      CrossrefPubMed
    • 2c Kitajima M, Mori I, Arai K, Kogure N, Takayama H. Tetrahedron Lett. 2006; 47: 3199
      Crossref
    • 2d Trost BM, Zhang Y. J. Am. Chem. Soc. 2006; 128: 4590
      CrossrefPubMed
    • 2e Bui T, Syed S, Barbas III CF. J. Am. Chem. Soc. 2009; 131: 8758
      CrossrefPubMed
    • 2f Guo C, Song J, Huang J.-Z, Chen P.-H, Luo S.-W, Gong L.-Z. Angew. Chem. Int. Ed. 2012; 51: 1046
      CrossrefPubMed

      For reviews on the asymmetric synthesis of 3-substituted oxindoles, see:
    • 3a Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
    • 3b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
    • 3c Trost BM, Brennan MK. Synthesis 2009; 3003
      Article in Thieme Connect
    • 3d Zhou F, Liu J.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381

      For selected examples of asymmetric Michael additions using oxindoles as nucleophiles, see ref. 2e and:
    • 4a Kato Y, Furutachi M, Chen Z, Mitsunuma H, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 9168
      Crossref
    • 4b He R, Shirakawa S, Maruoka K. J. Am. Chem. Soc. 2009; 131: 16620
      Crossref
    • 4c He R, Ding C, Maruoka K. Angew. Chem. Int. Ed. 2009; 48: 4559
      Crossref
    • 4d Galzerano P, Bencivenni G, Pesciaioli F, Mazzanti A, Giannichi B, Sambri L, Bartoli G, Melchiorre P. Chem.–Eur. J. 2009; 15: 7846
    • 4e Bravo N, Mon I, Companyó X, Alba A.-N, Moyano A, Rios R. Tetrahedron Lett. 2009; 50: 6624
      Crossref
    • 4f Zhu Q, Lu Y. Angew. Chem. Int. Ed. 2010; 49: 7753
      Crossref
    • 4g Liao Y.-H, Liu X.-L, Wu Z.-J, Cun L.-F, Zhang X.-M, Yuan W.-C. Org. Lett. 2010; 12: 2896
      CrossrefPubMed
    • 4h Li X, Luo S, Cheng J.-P. Chem.–Eur. J. 2010; 16: 14290
    • 4i Sun W, Hong L, Liu C, Wang R. Tetrahedron: Asymmetry 2010; 21: 2493
      Crossref
    • 4j Ding M, Zhou F, Liu Y.-L, Wang C.-H, Zhao X.-L, Zhou J. Chem. Sci. 2011; 2: 2035
      Crossref
    • 4k Freund MH, Tsogoeva SB. Synlett 2011; 503
      Article in Thieme Connect
    • 4l Zheng W, Zhang Z, Kaplan MJ, Antilla JC. J. Am. Chem. Soc. 2011; 133: 3339
      Crossref
    • 4m Duan S.-W, An J, Chen J.-R, Xiao W.-J. Org. Lett. 2011; 13: 2290
      CrossrefPubMed
    • 4n Tan B, Candeias NR, Barbas III CF. Nat. Chem. 2011; 3: 473
    • 4o Zhang T, Cheng L, Hameed S, Liu L, Wang D, Chen Y.-J. Chem. Commun. 2011; 47: 6644
      Crossref
    • 4p Bergonzini G, Melchiorre P. Angew. Chem. Int. Ed. 2012; 51: 971
      CrossrefPubMed
    • 4q Wang C, Yang X, Enders D. Chem.–Eur. J. 2012; 18: 4832
    • 4r Retini M, Bergonzini G, Melchiorre P. Chem. Commun. 2012; 48: 3336
      CrossrefPubMed
    • 4s Li L, Chen W, Yang W, Pan Y, Liu H, Tan C.-H, Jiang Z. Chem. Commun. 2012; 48: 5124
      CrossrefPubMed

      For selected examples of applications of maleimides in organocatalysis, see refs. 4g, 4s, and:
    • 5a 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
      CrossrefPubMed
    • 5b Shen J, Nguyen TT, Goh Y.-P, Ye W, Fu X, Xu J, Tan C.-H. J. Am. Chem. Soc. 2006; 128: 13692
      CrossrefPubMed
    • 5c Zhao G.-L, Xu Y, Sundén H, Eriksson L, Sayah M, Córdova A. Chem. Commun. 2007; 43: 734
    • 5d Zhu L, Xie H, Li H, Wang J, Jiang W, Wang W. Adv. Synth. Catal. 2007; 349: 1882
      Crossref
    • 5e Lu J, Zhou W.-J, Liu F, Loh T.-P. Adv. Synth. Catal. 2008; 350: 1796
      Crossref
    • 5f Gioia C, Hauville A, Bernardi L, Fini F, Ricci A. Angew. Chem. Int. Ed. 2008; 47: 9236
      CrossrefPubMed
    • 5g Soh JY.-T, Tan C.-H. J. Am. Chem. Soc. 2009; 131: 6904
      CrossrefPubMed
    • 5h 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
      CrossrefPubMed
    • 5i Xue F, Liu L, Zhang S, Duan W, Wang W. Chem.–Eur. J. 2010; 16: 7979
    • 5j Alba A.-NR, Valero G, Calbet T, Font-Bardía M, Moyano A, Rios R. Chem.–Eur. J. 2010; 16: 9884
    • 5k Yu F, Sun X, Jin Z, Wen S, Liang X, Ye J. Chem. Commun. (Cambridge) 2010; 46: 4589
      Crossref
    • 5l Yu F, Yin Z, Huang H, Ye T, Liang X, Ye J. Org. Biomol. Chem. 2010; 8: 4767
      Crossref
    • 5m Gómez-Torres E, Alonso DA, Gómez-Bengoa E, Nájera C. Org. Lett. 2011; 13: 6106
      Crossref
    • 5n Mazzanti A, Calbet T, Font-Bardia M, Moyano A, Rios R. Org. Biomol. Chem. 2012; 10: 1645
      Crossref

      For recent reviews on organocatalysis, see:
    • 6a Berkessel A, Gröger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis. Wiley-VCH; Weinheim: 2005
      CrossrefGoogle Scholar
    • 6b Enantioselective Organocatalysis: Reactions and Experimental Procedures. Dalko PI. Wiley-VCH; Weinheim: 2007
      CrossrefGoogle Scholar
    • 6c Special issue on Organocatalysis: Chem. Rev. 2007; 107: 5413
      Crossref
    • 6d Pellissier H. Tetrahedron 2007; 63: 9267
      Crossref
    • 6e Marcia de Figueiredo R, Christmann M. Eur. J. Org. Chem. 2007; 2575
    • 6f Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
      CrossrefPubMed
    • 6g Dondoni A, Massi A. Angew. Chem. Int. Ed. 2008; 47: 4638
      CrossrefPubMed
    • 6h Enders D, Narine AA. J. Org. Chem. 2008; 73: 7857
      CrossrefPubMed
    • 6i Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed. 2008; 47: 6138
      CrossrefPubMed
    • 6j Bertelsen S, Jørgensen KA. Chem. Soc. Rev. 2009; 38: 2178
      CrossrefPubMed
    • 6k Bella M, Gasperi T. Synthesis 2009; 1583
      Article in Thieme Connect
    • 6l Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
      CrossrefPubMed
    • 6m Merino P, Marqués-Lopéz E, Tejero T, Herrera RP. Synthesis 2010; 1
      Article in Thieme Connect
    • 6n Terada M. Synthesis 2010; 1929
      Article in Thieme Connect
    • 6o Albrecht Ł, Jiang H, Jørgensen KA. Angew. Chem. Int. Ed. 2011; 50: 8492
      CrossrefPubMed
    • 6p Pellissier H. Tetrahedron 2012; 68: 2197
      Crossref
    • 6q Giacalone F, Gruttadauria M, Agrigento P, Noto R. Chem. Soc. Rev. 2012; 41: 2406
      CrossrefPubMed
    • 6r Pellissier H. Adv. Synth. Catal. 2012; 354: 237
      Crossref
  • 7 For a review, see: Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
    CrossrefPubMed
  • 8 For a review, see: Erkkilä A, Majander I, Pihko PM. Chem. Rev. 2007; 107: 5416
    CrossrefPubMed

      • For selected examples on SOMO activation, see:
    • 9a Beeson TD, Mastracchio A, Hong J.-B, Ashton K, MacMillan DW. C. Science 2007; 316: 582
      CrossrefPubMed
    • 9b Sibi MP, Hasegawa M. J. Am. Chem. Soc. 2007; 129: 4124
      CrossrefPubMed
    • 9c Jang H.-Y, Hong J.-BMacMillan D. W. C. J. Am. Chem. Soc. 2007; 129: 7004
      Crossref
    • 9d Juli NT, Lee EC. Y, MacMillan DW. C. J. Am. Chem. Soc. 2010; 132: 10015
      Crossref
    • 9e Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011; 50: 951
      Crossref
    • 10a Russo A, Lattanzi A. Adv. Synth. Catal. 2008; 350: 1991
      Crossref
    • 10b Zheng C, Li Y, Yang Y, Wang H, Cui H, Zhang J, Zhao G. Adv. Synth. Catal. 2009; 351: 1685
      Crossref
    • 10c Palumbo C, Mazzeo G, Mazziotta A, Gambacorta A, Loreto MA, Migliorini A, Superchi S, Tofani D, Gasperi T. Org. Lett. 2011; 13: 6248
      Crossref
    • 11a Fang L, Lin A, Hu H, Zhu C. Chem.–Eur. J. 2009; 15: 7039
    • 11b Lin A, Fang L, Zhu X, Zhu C, Cheng Y. Adv. Synth. Catal. 2011; 353: 545
      Crossref
    • 12a Lattanzi A. Tetrahedron: Asymmetry 2006; 17: 837
      Crossref
    • 12b Russo A, Lattanzi A. Tetrahedron: Asymmetry 2010; 21: 1155
      Crossref
    • 12c Russo A, Capobianco A, Perfetto A, Lattanzi A, Peluso A. Eur. J. Org. Chem. 2011; 1922
    • 12d Russo A, Meninno S, Tedesco C, Lattanzi A. Eur. J. Org. Chem. 2011; 5096
    • 12e Lattanzi A, De Fusco C, Russo A, Poater A, Cavallo L. Chem. Commun. 2012; 48: 1650
      Crossref
  • 13 For details on the determination of the configuration of the products, see the Supporting Information.