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 Mroß; Simone Ladzik; Helmut Reinke; Anke Spannenberg; Christine Fischer; Peter Langer

doi:10.1055/s-0029-1216814

PAPER

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 Mroß^a, Simone Ladzik^a, Helmut Reinke^a, Anke Spannenberg^b, Christine Fischer^b, 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

Abstract

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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

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