Download PDF
Synthesis 2009(2): 297-305  
DOI: 10.1055/s-0028-1083287
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Synthesis of 2-(Aryloxythio)benzoates by the First [3+3] Cyclizations of 3-Aryloxythio-1-silyloxybuta-1,3-dienes with 3-Alkoxy-2-en-1-ones

Inam Iqbala, Muhammad Imrana, Alexander Villingera, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
b Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
Further Information

Publication History

Received 16 July 2008
Publication Date:
19 December 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

Functionalized 2-(aryloxythio)benzoates were regio­selectively prepared by the first [3+3] cyclizations of 3-aryloxythio-1-trimethylsilyloxybuta-1,3-dienes with 3-alkoxy-2-en-1-ones.

Key words

cyclizations - diaryl sulfides - regioselectivity - pyridines - silyl enol ethers

    References

  • 1a Behar V. Danishefsky SJ. J. Am. Chem. Soc.  1993,  115:  7017 
    Google Scholar
  • 1b Toste FD. Still IWJ. J. Am. Chem. Soc.  1995,  117:  7261 
    Google Scholar
  • 1c Davidson BS. Molinski TF. Barrows LR. Ireland CM. J. Am. Chem. Soc.  1991,  113:  4709 
    Google Scholar
  • 1d Mori Y. Taneda S. Hayashi H. Sakushima A. Kamata K. Suzuki AK. Yoshino S. Sakata M. Sagai M. Seki K.-i. Biol. Pharm. Bull.  2002,  25:  145 
    Google Scholar
  • 1e Davis RA. Sandoval IT. Concepcion GP. Moreira da Rocha R. Ireland CM. Tetrahedron  2003,  59:  2855 
    Google Scholar
  • 1f Liu H. Fujiwara T. Nishikawa T. Mishima Y. Nagai H. Shida T. Tachibana K. Kobayashi H. Mangindaan REP. Namikoshi M. Tetrahedron  2005,  61:  8611 
    Google Scholar
  • 1g Kaplan ML. Reents WD. Tetrahedron Lett.  1982,  23:  373 
    Google Scholar
  • 1h Hosoya Y. Adachi H. Nakamura H. Nishimura Y. Naganawa H. Tetrahedron Lett.  1996,  37:  9227 
    Google Scholar
  • See for example:
  • 2a Glass HB. Reid EE. J. Am. Chem. Soc.  1929,  51:  3428 
    Google Scholar
  • 2b Dougherty G. Hammond PD. J. Am. Chem. Soc.  1935,  57:  117 
    Google Scholar
  • For the trifluoromethane-sulfonic acid catalyzed sulfurization of cycloalkanes, see:
  • 2c Olah GA. Wang Q. Prakash GKS. J. Am. Chem. Soc.  1990,  112:  3697 
    Google Scholar
  • 3 Kemp DS. Carey RI. Dewan JC. Galakatos NG. Kerkman D. Leung S.-L. J. Org. Chem.  1989,  54:  1589 ; and references cited therein
    CrossrefGoogle Scholar
  • 4 Chua M. Hoyer H. Z. Naturforsch. B  1965,  20:  416 
    Google Scholar
  • 5a Baxter I. Ben-Haida A. Colquhoun HM. Hodge P. Kohnke FH. Williams DJ. Chem. Eur. J.  2000,  6:  4285 ; and references cited therein
    Google Scholar
  • 5b Campbell JR. J. Org. Chem.  1964,  29:  1830 
    Google Scholar
  • 6a Taniguchi N. J. Org. Chem.  2007,  72:  1241 
    Google Scholar
  • 6b Fernández-Rodríguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc.  2006,  128:  2180 
    Google Scholar
  • 6c Murata M. Buchwald SL. Tetrahedron  2004,  60:  7397 
    Google Scholar
  • 7a Gendre F. Yang M. Diaz P. Org. Lett.  2005,  7:  2719 
    Google Scholar
  • 7b Bates CG. Gujadhur RK. Venkataraman D. Org. Lett.  2002,  4:  2803 
    Google Scholar
  • 7c Rábai J.  Synthesis  1989,  523 
    Google Scholar
  • 8a Hilt G. Lüers S. Synthesis  2003,  1784 
    Google Scholar
  • 8b Hilt G. Lüers S. Harms K. J. Org. Chem.  2004,  69:  624 
    Google Scholar
  • 9a Chan T.-H. Brownbridge P. J. Am. Chem. Soc.  1980,  102:  3534 
    Google Scholar
  • 9b Brownbridge P. Chan T.-H. Brook MA. Kang GJ. Can. J. Chem.  1983,  61:  688 
    Google Scholar
  • 10 For a review of [3+3] cyclizations, see: Feist H. Langer P. Synthesis  2007,  327 
    Article in Thieme ConnectGoogle Scholar
  • 11 For a review of 1,3-bis(silyloxy)buta-1,3-dienes, see: Langer P. Synthesis  2002,  441 
    Article in Thieme ConnectGoogle Scholar
  • 12a Rashid MA. Reinke H. Langer P. Tetrahedron Lett.  2007,  48:  2321 
    Google Scholar
  • 12b Rashid MA. Rasool N. Adeel M. Reinke H. Fischer C. Langer P. Tetrahedron  2008,  64:  3782 
    Google Scholar
  • 13a Chan TH. Prasad CVC. J. Org. Chem.  1986,  51:  3012 
    Google Scholar
  • 13b Chan TH. Prasad CVC. J. Org. Chem.  1987,  52:  110 
    Google Scholar
  • 14 Rashid MA. Rasool N. Iqbal I. Iqbal I. Langer P. Tetrahedron Lett.  2008,  49:  2466 
    CrossrefGoogle Scholar
  • 15 Andersson C.-M. Hallberg A. J. Org. Chem.  1988,  53:  4257 
    CrossrefGoogle Scholar
16

CCDC-700707 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; Fax: +44(1223)336 033; or deposit@ccdc.cam.ac.uk.