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Communication | Regular issue | Vol 29, No. 3, 1989, pp.453-458
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4884
α-Allylation of β-Tetronic Acids and Chirality Transfer via the 4-Oxygenated 2(5H)-Furanone System

Takefumi Momose,* Naoki Toyooka, Hiromi Fujii, and Hironobu Yanagino

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan

Abstract

α-Allylation of the β-tetronate system was accomplished by direct attack of allyl halide on C-3 of the system in the presence of potassium carbonate in N,N-dimethylformamide or the Claisen rearrangement of allyl tetronates concomitantly formed in the preceding direct allylation. The chirality of natural L- amino acids was transferred into the β-tetronic acid system at the α-position via initial incorporation into the γ-position and subsequent α-allylation by application of analogous sequence of reactions.