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Synthesis 2011(14): 2281-2290  
DOI: 10.1055/s-0030-1260071
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

E/Z-Selective Synthesis of Alkylidene-3-oxo-3H-isobenzofurans by Reaction of Silyl Enol Ethers with Phthaloyl Dichloride

Satenik Mkrtchyana, Zorik Chilingaryana,b, Gagik Ghazaryana,b, Rüdiger Dedea, Nasir Rasoola,c, Muhammad A. Rashida, Alexander Villingera, Helmar Görlsd, Gnuni Karapetyana, Tariel V. Ghochikyanb, Ashot Saghiyanb,e, Peter Langer*a,f
a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
b Faculty of Chemistry, Yerevan State University, Alex Manoogian 1, 0025 Yerevan, Armenia
c Government College University, Faisalabad, Punjab, Pakistan
d Institut für Anorganische und Analytische Chemie, Universität Jena, August-Bebel-Str. 2, 07740 Jena, Germany
e CJSC Scientific Research Institute of Biotechnology, Gyurjyan Str. 14, 0056, Yerevan, Armenia
f 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 22 March 2011
Publication Date:
15 June 2011 (online)

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Abstract

The reaction of silyl enol ethers with phthaloyl dichloride afforded alkylidene-3-oxo-3H-isobenzofurans with very good E/Z-selectivity.

Key Words

cyclizations - O-heterocycles - phthalic acid derivatives - silyl enol ethers

    References

  • For reviews, see for example:
  • 1a Rao YS. Chem. Rev.  1976,  76:  625 
    Google Scholar
  • 1b Pattenden G. Prog. Chem. Nat. Prod.  1978,  35:  133 
    Google Scholar
  • 1c Gill M. Steglich W. Prog. Chem. Org. Nat. Prod.  1987,  51:  1 
    Google Scholar
  • 1d Knight DW. Contemp. Org. Synth.  1994,  1:  287 
    Google Scholar
  • 1e Negishi E.-i. Kotora M. Tetrahedron  1997,  53:  6707 
    Google Scholar
  • For reviews of syntheses of γ-alkylidenebutenolides, see:
  • 1f Brückner R. Chem. Commun.  2001,  141 
    Google Scholar
  • 1g Brückner R. Curr. Org. Chem.  2001,  5:  679 
    Google Scholar
  • 2a Rossi R. Bellina F. Biagetti M. Mannina L. Tetrahedron Lett.  1998,  39:  7799 
    Google Scholar
  • 2b Xu C. Negishi E.-i. Tetrahedron Lett.  1999,  40:  431 
    Google Scholar
  • 3a Siegel K. Brückner R. Chem. Eur. J.  1998,  4:  1116 
    Google Scholar
  • 3b Görth FC. Brückner R. Synthesis  1999,  1520 
    Google Scholar
  • 4a Goerth F. Umland A. Brückner R. Eur. J. Org. Chem.  1998,  1055 
    Google Scholar
  • 4b v. d. Ohe F. Brückner R. Tetrahedron Lett.  1998,  39:  1909 
    Google Scholar
  • 4c Hanisch I. Brückner R. Synlett  2000,  374 
    Google Scholar
  • 5a Ingham CF. Massy-Westropp RA. Reynolds GD. Thorpe WD. Aust. J. Chem.  1975,  28:  2499 
    Google Scholar
  • 5b Knight DW. Pattenden G. J. Chem. Soc., Perkin Trans. 1  1979,  62 
    Google Scholar
  • 6 Albrecht U. Nguyen VTH. Langer P. Synthesis  2006,  1111 
    Article in Thieme ConnectGoogle Scholar
  • 7 For a review of 1,3-bis(silyl enol ethers), see: Langer P. Synthesis  2002,  441 
    Google Scholar
  • 8 For a review of cyclizations of 1,3-bis(silyl enol ethers) with oxalyl chloride, see: Langer P. Synlett  2006,  3369 
    Article in Thieme ConnectGoogle Scholar
  • 9a Naito T. Katsuhara T. Niitsu K. Ikeya Y. Okada M. Mitsuhashi H. Phytochemistry  1992,  31:  639 
    Google Scholar
  • 9b Hagemaier J. Batz O. Schmidt J. Wray V. Hahlbrock K. Strack D. Phytochemistry  1999,  51:  629 
    Google Scholar
  • 9c Pushan W. Xuanliang G. Yixiong W. Fukuyama Y. Miura I. Sugawara M. Phytochemistry  1984,  23:  2033 
    Google Scholar
  • 9d Bellina F. Ciucci D. Vergamini P. Rossi R. Tetrahedron  2000,  56:  2533 
    Google Scholar
  • 9e Li S. Wang Z. Fang X. Yang Y. Li Y. Synth. Commun.  1997,  27:  1783 
    Google Scholar
  • 9f Kobayashi M. Mitsuhashi H. Chem. Pharm. Bull.  1987,  35:  4789 
    Google Scholar
  • 9g Kobayashi M. Fujita M. Mitsuhashi H. Chem. Pharm. Bull.  1987,  35:  1427 
    Google Scholar
  • 10a Yoshikawa M. Uchida E. Chatani N. Murakami N. Yamahara J. Chem. Pharm. Bull.  1992,  40:  3121 
    Google Scholar
  • 10b Umehara K. Matsumoto M. Nakamura M. Miyase T. Kuroyanagi M. Noguchi H. Chem. Pharm. Bull.  2000,  48:  566 
    Google Scholar
  • 11 Zhang G.-L. Ruecker G. Breitmaier E. Nieger M. Mayer R. Steinbeck C. Phytochemistry  1995,  40:  299 
    CrossrefGoogle Scholar
  • 12a Ruggli P. Zickendraht C. Helv. Chim. Acta  1945,  28:  1377 
    Google Scholar
  • 12b Bülow R. Koch S. Ber. Dtsch. Chem. Ges.  1904,  37:  579 
    Google Scholar
  • 12c Scheiber J. Justus Liebigs Ann. Chem.  1912,  389:  151 
    Google Scholar
  • 12d Maruyama K. Osuka A. J. Org. Chem.  1980,  45:  1898 
    Google Scholar
  • For reactions of pseudophthaloyl chloride, see:
  • 12e Naik SN. Pandey B. Ayyangar NR. Synth. Commun.  1988,  18:  625 
    Google Scholar
  • 13a Chordia MD. Narasimhan NS. J. Chem. Soc., Perkin Trans. 1  1991,  371 
    Google Scholar
  • 13b Hanack M. Zipplies T. J. Am. Chem. Soc.  1985,  107:  6127 
    Google Scholar
  • 13c Kayser MM. Hatt KL. Hooper DL. Can. J. Chem.  1992,  70:  1985 
    Google Scholar
  • 13d Abell AD. Hoult DA. Morris KM. Taylor JM. Trent JO. J. Org. Chem.  1993,  58:  1531 
    Google Scholar
  • 14 Kundu NG. Pal M. J. Chem. Soc., Chem. Commun.  1993,  86 
    Google Scholar
  • 17 Fischer E. Koch H. Ber. Dtsch. Chem. Ges.  1883,  16:  651 
    CrossrefGoogle Scholar
  • 18 Kundu NG. Pal M. Nandi B. J. Chem. Soc., Perkin Trans. 1  1998,  561 
    Google Scholar
  • 19 Renfrew AH. Bostock SB. J. Chem. Soc., Perkin Trans. 1  1977,  84 
    Google Scholar
15

For the AlCl3-catalyzed transformation of 1 into A, see ref. 12e.

16

CCDC-821844 (5i), CCDC-823020 (5f), CCDC-823021 (6a), and CCDC-824363 (7a) contain all crystallographic details of this publication and are 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 CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.