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Synthesis 2009(13): 2236-2248  
DOI: 10.1055/s-0029-1216814
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized Salicylates by Formal [3+3] Cyclocondensation of 1,3-Bis(silyloxy)buta-1,3-dienes with 3-Alkoxy-2-en-1-ones

Gerson Mroßa, Simone Ladzika, Helmut Reinkea, Anke Spannenbergb, Christine Fischerb, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 6 September 2008
Publication Date:
25 May 2009 (online)

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Abstract

The formal [3+3] cyclization of 1,3-bis(silyloxy)buta-1,3-dienes with 1-aryl-3-ethoxyprop-2-en-1-ones, available by Heck reaction of benzoyl chlorides with ethyl vinyl ether, afforded a variety of 6-arylsalicylates. The reaction of the products with concentrated sulfuric acid resulted in the formation of fluorenones. 6-Alkylsalicylates were prepared by cyclization of 1,3-bis(silyl­oxy)buta-1,3-dienes with aliphatic enones.

Key words

arenes - cyclizations - palladium - regioselectivity - silyl enol ethers

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CCDC-725263 and CCDC-725731 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.