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Synlett 2011(19): 2834-2840  
DOI: 10.1055/s-0031-1289879
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective γ-Olefination of Substituted Cyclobutenediones by Organocatalysis

Mallesh Beesu, Mariappan Periasamy*
School of Chemistry, University of Hyderabad, Hyderabad 500046, A.P., India
Fax: +91(40)23012460; e-Mail: mpsc@uohyd.ernet.in;
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Publication History

Received 13 August 2011
Publication Date:
11 November 2011 (online)

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Abstract

Methods are described for the stereoselective synthesis of alkenyl-substituted cyclobutenediones from alkyl-substituted cyclobutenediones and aldehydes in 70-91% yields using pyrrolidine as catalyst under mild reaction conditions.

Key words

cyclobutenediones - γ-olefination - organocatalysis

    References and Notes

  • 1a Jewell CF. Liebeskind LS. Williamson M. J. Am. Chem. Soc.  1985,  107:  6715 
    Search in Google Scholar
  • 1b Liebeskind LS. Iyer S. Jewell CF. J. Org. Chem.  1986,  51:  3065 
    Search in Google Scholar
  • 1c Liebeskind LS. Bombrum A. J. Org. Chem.  1994,  59:  6856 
    Search in Google Scholar
  • 1d Shi X. Amin R. Liebeskind LS. J. Org. Chem.  2000,  65:  1650 
    Search in Google Scholar
  • 1e Shi X. Liebeskind LS. J. Org. Chem.  2000,  65:  1665 
    Search in Google Scholar
  • 1f Pena-Cabrera E. Liebeskind LS.
    J. Org. Chem.  2002,  67:  1689 
    Search in Google Scholar
  • 1g Aguilar-Aguilar AL. Liebeskind LS. Pena-Cabrera E. J. Org. Chem.  2007,  72:  8539 
    Search in Google Scholar
  • 2a Karlsson JO. Nguyen NV. Foland LD. Moore HW. J. Am. Chem. Soc.  1985,  107:  3392 
    Search in Google Scholar
  • 2b Moore HW. Decker OH. Chem. Rev.  1986,  86:  821 
    Search in Google Scholar
  • 2c Lee KH. Moore HW. J. Org. Chem.  1995,  60:  735 
    Search in Google Scholar
  • 2d Taing M. Moore HW. J. Org. Chem.  1996,  61:  329 
    Search in Google Scholar
  • 3a Negri JT. Morwick T. Doyon J. Wilson PD. Hickey ER. Paquette LA. J. Am. Chem. Soc.  1993,  115:  12189 
    Search in Google Scholar
  • 3b Paquette LA. Morwick TM. J. Am. Chem. Soc.  1997,  119:  1230 
    Search in Google Scholar
  • 3c Paquette LA. Kuo LH. Tae J. J. Org. Chem.  1998,  63:  2010 
    Search in Google Scholar
  • 3d Geng F. Liu J. Paquette LA. Org. Lett.  2002,  4:  71 
    Search in Google Scholar
  • 4a Danheiser RL. Gee SK. Sard H. J. Am. Chem. Soc.  1982,  104:  7670 
    Search in Google Scholar
  • 4b Danheiser RL. Gee SK. J. Org. Chem.  1984,  49:  1672 
    Search in Google Scholar
  • 4c Danheiser RL. Gee SK. Perez JJ. J. Am. Chem. Soc.  1986,  108:  806 
    Search in Google Scholar
  • 5a Renard BC. Aubert Y. Asseline U. Tetrahedron Lett.  2009,  50:  1897 
    Search in Google Scholar
  • 5b Planty B. Pujol C. Lamothe M. Maraval C. Horn C. Grand BL. Perez M. Bioorg. Med. Chem. Lett.  2010,  20:  1735 
    Search in Google Scholar
  • 6 Shi X. Amin SR. Liebeskind LS. J. Org. Chem.  2000,  65:  1650 
    Search in Google Scholar
  • 7a MacDougall JM. Moore HW. J. Org. Chem.  1999,  64:  7445 
    Search in Google Scholar
  • 7b MacDougall JM. Moore HW. J. Org. Chem.  1997,  62:  4554 
    Search in Google Scholar
  • 8 Avirah RR. Jyothish K. Ramaiah D. Org. Lett.  2007,  9:  121 
    Search in Google Scholar
  • 9a Jyothish K. Arun KT. Ramaiah D. Org. Lett.  2004,  6:  3965 
    Search in Google Scholar
  • 9b Jyothish K. Avirah RR. Ramaiah D. Org. Lett.  2006,  8:  111 
    Search in Google Scholar
  • 9c Volkova KD. Kovalska VB. Tatarets AL. Patsenker LD. Kryvorotenko DV. Yarmoluk SM. Dyes Pigm.  2007,  72:  285 
    Search in Google Scholar
  • 10 Shinada T. Ooyama Y. Hayashi K.-I. Ohfune Y. Tetrahedron Lett.  2002,  43:  6755 
    Search in Google Scholar
  • 11 John A. Butera JA. Jenkins DJ. Lennox JR. Sheldon JH. Norton NW. Warga D. Argentierib TM. Bioorg. Med. Chem. Lett.  2005,  15:  2495 
    Search in Google Scholar
  • 12 Ried W. Vogl M. Chem. Ber.  1982,  115:  403 
    Search in Google Scholar
  • 13a Periasamy M. Radhakrishnan U. Brunet JJ. Chauvin R. Elzaizi A. J. Chem. Soc., Chem. Commun.  1996,  1499 
  • 13b Rameshkumar C. Periasamy M. Synlett  2000,  1619 
  • 13c Periasamy M. Rameshkumar C. Mukkanti A. J. Organomet. Chem.  2002,  649:  209 
    Search in Google Scholar
  • 13d Rameshkumar C. Periasamy M. Organometallics  2000,  19:  2400 
    Search in Google Scholar
  • 13e Periasamy M. Rameshkumar C. Radhakrishnan U. Tetrahedron Lett.  1997,  38:  7229 
    Search in Google Scholar
  • 13f Rameshkumar C. Periasamy M. Tetrahedron Lett.  2000,  41:  2719 
    Search in Google Scholar
  • 13g Periasamy M. Mukkanti A. Shyam Raj D. Organometallics  2004,  23:  6323 
    Search in Google Scholar
  • 13h Periasamy M. Beesu M. Shyam Raj D. J. Organomet. Chem.  2008,  693:  2843 
    Search in Google Scholar
  • 13i Periasamy M. Mukkanti A. Shyam Raj D. Organometallics  2004,  23:  619 
    Search in Google Scholar
  • 13j Periasamy M. Rameshkumar C. Radhakrishnan U. Brunet JJ. J. Org. Chem.  1998,  63:  4930 
    Search in Google Scholar
  • 13k Beesu M. Periasamy M. J. Org. Chem.  2011,  76:  543 
    Search in Google Scholar
  • For selected organocatalysis reviews, see:
  • 14a Dalko PI. Moisan L. Angew. Chem. Int. Ed.  2001,  40:  3726 
    Search in Google Scholar
  • 14b List B. Tetrahedron  2002,  58:  5573 
    Search in Google Scholar
  • 14c Notz W. Tanaka F. Barbas CF. Acc. Chem. Res.  2004,  37:  580 
    Search in Google Scholar
  • 14d Dalko PI. Moisan L. Angew. Chem. Int. Ed.  2004,  43:  5138 
    Search in Google Scholar
  • 14e Enders D. Grondal C. Huttl MRM. Angew. Chem. Int. Ed.  2007,  46:  1570 
    Search in Google Scholar
  • 14f Erkkila A. Majander I. Pihko PM. Chem. Rev.  2007,  107:  5416 
    Search in Google Scholar
  • 14g Bertelsen S. Jørgensen KA. Chem. Soc. Rev.  2009,  38:  2178 
    Search in Google Scholar
  • 15a List B. Lerner RA. Barbas CF. J. Am. Chem. Soc.  2000,  122:  2395 
    Search in Google Scholar
  • 15b Bertelsen S. Marigo M. Brandes S. Diner P. Jørgensen KA. J. Am. Chem. Soc.  2006,  128:  12973 
    Search in Google Scholar
  • 15c Utsumi N. Zhang H. Tanaka F. Barbas CF. Angew. Chem. Int. Ed.  2007,  46:  1878 
    Search in Google Scholar
  • 15d Zhao GL. Rios R. Vesely J. Eriksson L. Cordova A. Angew. Chem. Int. Ed.  2008,  47:  8468 
    Search in Google Scholar
  • 15e Ramachary DB. Ramakumar K. Narayana VV. Chem. Eur. J.  2008,  14:  9143 
    Search in Google Scholar
  • 15f Han B. Xiao Y. He Z. Chen Y. Org. Lett.  2009,  11:  4660 
    Search in Google Scholar
  • 15g Han B. He Z. Li J. Li R. Jiang K. Liu T. Chen Y. Angew. Chem. Int. Ed.  2009,  48:  5474 
    Search in Google Scholar
  • 15h Humbeck JFV. Simonovich SP. Knowles RR. MacMillan DWC. J. Am. Chem. Soc.  2010,  132:  10012 
    Search in Google Scholar
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CCDC 809408 (3a), 809409 (3k), and 809407 (4a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif