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

Satenik Mkrtchyan; Zorik Chilingaryan; Gagik Ghazaryan; Rüdiger Dede; Nasir Rasool; Muhammad A. Rashid; Alexander Villinger; Helmar Görls; Gnuni Karapetyan; Tariel V. Ghochikyan; Ashot Saghiyan; Peter Langer

doi:10.1055/s-0030-1260071

PAPER

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

Satenik Mkrtchyan^a, Zorik Chilingaryan^a,b, Gagik Ghazaryan^a,b, Rüdiger Dede^a, Nasir Rasool^a,c, Muhammad A. Rashid^a, Alexander Villinger^a, Helmar Görls^d, Gnuni Karapetyan^a, Tariel V. Ghochikyan^b, Ashot Saghiyan^b,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;

Abstract

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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

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Referenzen

References

For reviews, see for example:

<A NAME="RN32001SS-1A">1a</A> Rao YS. Chem. Rev. 1976, 76: 625

<A NAME="RN32001SS-1B">1b</A> Pattenden G. Prog. Chem. Nat. Prod. 1978, 35: 133

<A NAME="RN32001SS-1C">1c</A> Gill M. Steglich W. Prog. Chem. Org. Nat. Prod. 1987, 51: 1

<A NAME="RN32001SS-1D">1d</A> Knight DW. Contemp. Org. Synth. 1994, 1: 287

<A NAME="RN32001SS-1E">1e</A> Negishi E.-i. Kotora M. Tetrahedron 1997, 53: 6707

For reviews of syntheses of γ-alkylidenebutenolides, see:

<A NAME="RN32001SS-1F">1f</A> Brückner R. Chem. Commun. 2001, 141

<A NAME="RN32001SS-1G">1g</A> Brückner R. Curr. Org. Chem. 2001, 5: 679

<A NAME="RN32001SS-2A">2a</A> Rossi R. Bellina F. Biagetti M. Mannina L. Tetrahedron Lett. 1998, 39: 7799

<A NAME="RN32001SS-2B">2b</A> Xu C. Negishi E.-i. Tetrahedron Lett. 1999, 40: 431

<A NAME="RN32001SS-3A">3a</A> Siegel K. Brückner R. Chem. Eur. J. 1998, 4: 1116

<A NAME="RN32001SS-3B">3b</A> Görth FC. Brückner R. Synthesis 1999, 1520

<A NAME="RN32001SS-4A">4a</A> Goerth F. Umland A. Brückner R. Eur. J. Org. Chem. 1998, 1055

<A NAME="RN32001SS-4B">4b</A> v. d. Ohe F. Brückner R. Tetrahedron Lett. 1998, 39: 1909

<A NAME="RN32001SS-4C">4c</A> Hanisch I. Brückner R. Synlett 2000, 374

<A NAME="RN32001SS-5A">5a</A> Ingham CF. Massy-Westropp RA. Reynolds GD. Thorpe WD. Aust. J. Chem. 1975, 28: 2499

<A NAME="RN32001SS-5B">5b</A> Knight DW. Pattenden G. J. Chem. Soc., Perkin Trans. 1 1979, 62

<A NAME="RN32001SS-6">6</A> Albrecht U. Nguyen VTH. Langer P. Synthesis 2006, 1111

<A NAME="RN32001SS-7">7</A> For a review of 1,3-bis(silyl enol ethers), see: Langer P. Synthesis 2002, 441

<A NAME="RN32001SS-8">8</A> For a review of cyclizations of 1,3-bis(silyl enol ethers) with oxalyl chloride, see: Langer P. Synlett 2006, 3369

<A NAME="RN32001SS-9A">9a</A> Naito T. Katsuhara T. Niitsu K. Ikeya Y. Okada M. Mitsuhashi H. Phytochemistry 1992, 31: 639

<A NAME="RN32001SS-9B">9b</A> Hagemaier J. Batz O. Schmidt J. Wray V. Hahlbrock K. Strack D. Phytochemistry 1999, 51: 629

<A NAME="RN32001SS-9C">9c</A> Pushan W. Xuanliang G. Yixiong W. Fukuyama Y. Miura I. Sugawara M. Phytochemistry 1984, 23: 2033

<A NAME="RN32001SS-9D">9d</A> Bellina F. Ciucci D. Vergamini P. Rossi R. Tetrahedron 2000, 56: 2533

<A NAME="RN32001SS-9E">9e</A> Li S. Wang Z. Fang X. Yang Y. Li Y. Synth. Commun. 1997, 27: 1783

<A NAME="RN32001SS-9F">9f</A> Kobayashi M. Mitsuhashi H. Chem. Pharm. Bull. 1987, 35: 4789

<A NAME="RN32001SS-9G">9g</A> Kobayashi M. Fujita M. Mitsuhashi H. Chem. Pharm. Bull. 1987, 35: 1427

<A NAME="RN32001SS-10A">10a</A> Yoshikawa M. Uchida E. Chatani N. Murakami N. Yamahara J. Chem. Pharm. Bull. 1992, 40: 3121

<A NAME="RN32001SS-10B">10b</A> Umehara K. Matsumoto M. Nakamura M. Miyase T. Kuroyanagi M. Noguchi H. Chem. Pharm. Bull. 2000, 48: 566

<A NAME="RN32001SS-11">11</A> Zhang G.-L. Ruecker G. Breitmaier E. Nieger M. Mayer R. Steinbeck C. Phytochemistry 1995, 40: 299

<A NAME="RN32001SS-12A">12a</A> Ruggli P. Zickendraht C. Helv. Chim. Acta 1945, 28: 1377

<A NAME="RN32001SS-12B">12b</A> Bülow R. Koch S. Ber. Dtsch. Chem. Ges. 1904, 37: 579

<A NAME="RN32001SS-12C">12c</A> Scheiber J. Justus Liebigs Ann. Chem. 1912, 389: 151

<A NAME="RN32001SS-12D">12d</A> Maruyama K. Osuka A. J. Org. Chem. 1980, 45: 1898

For reactions of pseudophthaloyl chloride, see:

<A NAME="RN32001SS-12E">12e</A> Naik SN. Pandey B. Ayyangar NR. Synth. Commun. 1988, 18: 625

<A NAME="RN32001SS-13A">13a</A> Chordia MD. Narasimhan NS. J. Chem. Soc., Perkin Trans. 1 1991, 371

<A NAME="RN32001SS-13B">13b</A> Hanack M. Zipplies T. J. Am. Chem. Soc. 1985, 107: 6127

<A NAME="RN32001SS-13C">13c</A> Kayser MM. Hatt KL. Hooper DL. Can. J. Chem. 1992, 70: 1985

<A NAME="RN32001SS-13D">13d</A> Abell AD. Hoult DA. Morris KM. Taylor JM. Trent JO. J. Org. Chem. 1993, 58: 1531

<A NAME="RN32001SS-14">14</A> Kundu NG. Pal M. J. Chem. Soc., Chem. Commun. 1993, 86

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

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.

<A NAME="RN32001SS-17">17</A> Fischer E. Koch H. Ber. Dtsch. Chem. Ges. 1883, 16: 651

<A NAME="RN32001SS-18">18</A> Kundu NG. Pal M. Nandi B. J. Chem. Soc., Perkin Trans. 1 1998, 561

<A NAME="RN32001SS-19">19</A> Renfrew AH. Bostock SB. J. Chem. Soc., Perkin Trans. 1 1977, 84