Regioselectivity in the 1,3-Dipolar Cycloaddition Reaction of Pyridinium Dicyanomethylides with Unsymmetric Alkynes

DOI: 10.1246/cl.1987.807

Source and publish data:

Chemistry Letters p. 807 - 808 (1987)

Update date:2022-08-05

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Authors:

Matsumoto, Kiyoshi

Uchida, Takane

Konishi, Hideyuki

Watanabe, Youko

Aoyama, Kinuyo

Asahi, Momoyo

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Article abstract of DOI:10.1246/cl.1987.807

Representative pyridinium dicyanomethylides underwent regioselectively 1,3-dipolar cycloaddition onto methyl 3-trimethylsilyl-2-propynate and methyl 3-phenyl-2-propynate yielding the corresponding indolizines whereby 1-methoxycarbonylindolizines forms either exclusively or predominantly, in agreement with HOMO(ylide)-LUMO(dipolarophile) interaction as revealed by CNDO/2 calculation.

Full text of DOI:10.1246/cl.1987.807

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