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Communication | Special issue | Vol 49, No. 1, 1998, pp.73-78
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S35
Intramolecular [2+2] Photocycloaddition of Fumaramic Acid Ester Derivatives. Syntheses of 2-(2,3-Dicarboxycyclobutyl)glycines

Hidekazu Tsujishima, Keiko Shimamoto, Yasushi Shigeri, Noboru Yumoto, and Yasufumi Ohfune*

*Department of Material Science, Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan

Abstract

Two isomers of new glutamate analogs, (2S,1’R,2’R,3’S)- and (2S,1’R,2’R,3’S)-2-(2,3-dicarboxycyclobutyl)glycines (1a) and (1b), are synthesized from the novel 3-azabicyclo[3.1.1]heptan-2-one intermediates (5a) and (5b), respectively, via an intramolecular photocycloaddition of α,β-unsaturated amide ester (3).