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Communication | Regular issue | Vol 27, No. 11, 1988, pp.2557-2562
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4733
Site Selectivity in the 1,3-Dipolar Cycloaddition Reaction of Unsymmetric Pyridinium Bis(methoxycarbonyl)methylides with Methyl Propiolate

Kiyoshi Matsumoto,* Yukio Ikemi, Hideyuki Konishi, Xiao-lan Shi, and Takane Uchida

*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan


The 1,3-dipolar cycloaddition of.unsymmetric pyridinium bis(methoxycarbonyl)methylides with methyl propiolate proceeds in moderate to good yields with high to moderate site selectivity with respect to the ylide. Polar 3-substituted pyridinium bis(methoxycarbonyl)methlides generally gave predominantly the corresponding 8-substituted indolizines regardless of the substituents. The results can be explained by dipole-dipole interactions.