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Synthesis 2009(13): 2223-2235  
DOI: 10.1055/s-0029-1216801
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diversity-Oriented Synthesis of Functionalized Diaryl Sulfones by Regio­selective [3+3] Cyclizations of 1,3-Bis(siloxy)buta-1,3-dienes with 2-(Aryl­sulfonyl)-3-ethoxy-2-en-1-ones: Scope and Limitations

Mohanad Shkoora, Abdolmajid Riahia,b, Olumide Fatunsina, Helmut Reinkea, Christine Fischerb, 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
e-Mail: peter.langer@uni-rostock.de;
Further Information

Publication History

Received 15 January 2009
Publication Date:
12 May 2009 (online)

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Abstract

The formal [3+3] cyclization of 1,3-bis(siloxy)buta-1,3-dienes with 2-(arylsulfonyl)-3-ethoxy-2-en-1-ones, readily available by reaction of β-keto sulfones with triethyl orthoformate, allows the synthesis of a variety of functionalized diaryl sulfones with very good regioselectivity.

Key words

arenes - sulfones - cyclizations - regioselectivity - silyl enol ethers

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All crystallographic details of this publication are contained in CCDC-717949 (4ae) and CCDC-717950 (4d), 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.