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†,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

Organic & Biomolecular Chemistry Pub Date : 12/18/2009 00:00:00 , DOI:10.1039/B918466J

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.