Efficient synthesis of gamma-alkylidenetetronic esters by sequential Lewis acid catalyzed

¹Institut für Anorganische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany. planger@uni-goettingen.de

|April 3, 2001

Abstract:

A new approach for the synthesis of gamma-alkylidenetetronic acids and esters is reported which involves Me3SiOTf-catalyzed, regio- and stereoselective cyclization of 4-alkoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride. The alpha-hydroxy group of the butenolides is efficiently functionalized by palladium-catalyzed cross-coupling reactions via the corresponding enol triflates.

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Abstract:

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