Synthesis of 3-hydroxy-5-alkoxyhomophthalates by domino ‘2 : 1-coupling/intramolecular aldol condensation’ reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with tetraalkoxymethanes

Mathias Lubbe; Peter Langer

doi:10.1039/B918466J

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Synthesis of 3-hydroxy-5-alkoxyhomophthalates by domino ‘2 : 1-coupling/intramolecular aldol condensation’ reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with tetraalkoxymethanes†

Mathias Lubbe^a and Peter Langer*^ab

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* Corresponding authors

^a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, Rostock, Germany
E-mail: peter.langer@uni-rostock.de
Fax: 00 49 381 49864112
Tel: 00 49 381 4986410

^b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, Rostock, Germany

Abstract

The first domino ‘2 : 1 condensation/intramolecular aldol’ reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadiene with tetraalkoxymethanes provide a convenient approach to 3-hydroxy-5-alkoxyhomophthalates. These products, which contain one free and one protected hydroxyl group, can be functionalized by palladium(0)-catalyzed cross-coupling reactions.

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Supplementary files

Copies of NMR spectra PDF (2395K)

Article information

DOI: https://doi.org/10.1039/B918466J
Article type: Paper
Submitted: 08 Sep 2009
Accepted: 20 Nov 2009
First published: 18 Dec 2009

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Org. Biomol. Chem., 2010,8, 881-885

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Synthesis of 3-hydroxy-5-alkoxyhomophthalates by domino ‘2 : 1-coupling/intramolecular aldol condensation’ reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with tetraalkoxymethanes

M. Lubbe and P. Langer, Org. Biomol. Chem., 2010, 8, 881 DOI: 10.1039/B918466J

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Organic & Biomolecular Chemistry