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Synthesis 2009(13): 2236-2248
DOI: 10.1055/s-0029-1216814
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
Further Information
Received
6 September 2008
Publication Date:
25 May 2009 (online)
Publication History
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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References
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.