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SYNTHESIS OF SPIROPYRROLIDINES AND SPIROPYRROLIZIDINES FROM AZOMETHINE YLIDES

И. Н. Клочкова, М. П. Щекина, А. А. Аниськов
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Abstract


This is the first report of the use of asymmetrical cross‑conjugated unsaturated ketones as dipolarophiles in 1,3‑dipolar cycloaddition reactions. These reactions proceed without chemoselectivity at the two nonequivalent reaction sites of the dienone but diastereoselectively to give a mixture of structural isomers of endo‑cycloaddition products. Monoenones were used to synthesize spiropyrrolidizines with high diastereoselectivity.

How to Cite
Klochkova, I. N.; Shchekina, M. P.; Anis'kov, A. A. Chem. Heterocycl. Compd. 2014, 50, 479. [Khim. Geterotsikl. Soedin. 2014, 527.]

For this article in the English edition see DOI 10.1007/s10593-014-1498-z


Keywords


azomethine ylides; unsaturated ketones; 1,3 dipolar cycloaddition

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