Download PDF
Synthesis 2013; 45(18): 2520-2524
DOI: 10.1055/s-0033-1338505
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Synthesis of Spiro-cyclopropaneoxindoles

Artur Noole
a   Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia
,
Andrei V. Malkov
b   Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UK   Fax: +3726202828   Email: kanger@chemnet.ee
,
Tõnis Kanger*
a   Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia
› Author Affiliations
Further Information

Publication History

Received: 23 May 2013

Accepted after revision: 21 June 2013

Publication Date:
23 July 2013 (online)

    Permissions and Reprints All articles of this category


Abstract

Straightforward cascade reactions for the synthesis of spiro-cyclopropaneoxindoles are described. The target compounds are obtained in high yields and in good enantio- and diastereoselectivities via hydrogen bonding or iminium catalysis.

Key words

spiro compounds - organocatalysis - oxindoles - 3-chlorooxindoles - asymmetric synthesis

Supporting Information

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

  • References

    • 1a Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
      Crossref
    • 1b Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
      CrossrefPubMed
    • 2a 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
    • 2b He Y, Jiang T, Kuhen KL, Ellis DA, Wu B, Wu TY.-H, Bursulaya B. WO2004037247, 2004 ; Chem. Abstr. 2004, 140, 386004.
    • 3a Sampson PB, Liu Y, Li S.-W, Forrest BT, Pauls HW, Edwards LG, Feher M, Patel NK. B, Laufer R, Pan G. WO2010115279 A1, 2010 ; Chem. Abstr. 2010, 153, 480843.
    • 3b Pauls HW, Li S.-W, Sampson PB, Forrest BT. WO2012048411, 2012 ; Chem. Abstr. 2012, 156, 533898.
  • 4 Rottmann M, McNamara C, Yeung BK. S, Lee MC. S, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, Gonzalez-Paez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck HP, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science 2010; 329: 1175
    CrossrefPubMed
  • 5 Pesciaioli F, Righi P, Mazzanti A, Bartoli G, Bencivenni G. Chem. Eur. J. 2011; 17: 2842
    Crossref
  • 6 Dou X, Lu Y. Chem. Eur. J. 2012; 18: 8315
    Crossref
  • 7 Rios R, Sunden H, Vesely J, Zhao G.-L, Dziedzic P, Cordova A. Adv. Synth. Catal. 2007; 349: 1028
    Crossref
  • 8 Noole A, Järving I, Werner F, Lopp M, Malkov A, Kanger T. Org. Lett. 2012; 14: 4922
    Crossref
    • 9a Noole A, Sucman NS, Kabeshov MA, Kanger T, Macaev FZ, Malkov AV. Chem. Eur. J. 2012; 18: 14929
      Crossref
    • 9b Noole A, Ošeka M, Pehk T, Öeren M, Järving I, Elsegood MR. J, Malkov AV, Lopp M, Kanger T. Adv. Synth. Catal. 2013; 355: 829
      Crossref
    • 10a Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
      CrossrefPubMed
    • 10b McGilvra JD, Gondi VB, Rawal VH In Enantioselective Organocatalysis . Dalko PI. Wiley-VCH; Weinheim: 2007: 189-254
      CrossrefGoogle Scholar
    • 10c Connon SJ. Chem. Commun. 2008; 2499
    • 10d Alemán J, Parra A, Jiang H, Jørgensen KA. Chem. Eur. J. 2011; 17: 6890
      Crossref
  • 11 CCDC 916343 contains the supplementary crystallographic data for compound 9c. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.