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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;
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Publikationsverlauf

Received 22 March 2011
Publikationsdatum:
15. Juni 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

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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.