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Z. Naturforsch. 2013,
68b, 836 – 840
doi:10.5560/ZNB.2013-3060
4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of γ-Alkylidenetetronic Acids
1 Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
2 VNU University of Science, 334 Nguyen Trai, Thanh Xuan, Hanoi, Vietnam
3 Leibniz-Institut für Katalyse an der Universität Rostock e. V. (LIKAT), Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Reprint requests to Prof. Peter Langer. Fax: +381 4986412. E-mail:
peter.langer@uni-rostock.de
Received February 20, 2013 / published online July 19, 2013
A new approach to γ-alkylidenetetronic acids is reported which is based on Me3SiOTf-catalyzed [3 + 2] cyclization of 4-tert-butoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with oxalyl chloride, orthogonal protection of the α-hydroxy group by benzylation and subsequent deprotection of the β-hydroxy group.
Key words: Butenolides, Cyclizations, O-Heterocycles, Oxalic Acid, Silyl Enol Ethers