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Synthesis of Spiropyrrolidines and Spiropyrrolizidines from Azomethine Ylides

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, 83 Astrakhanskaya St., 410012, Saratov, Russia

    I. N. Klochkova, M. P. Shchekina & A. A. Anis’kov

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  1. I. N. Klochkova
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  2. M. P. Shchekina
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  3. A. A. Anis’kov
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Correspondence to A. A. Anis’kov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 527-536, April, 2014.

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Klochkova, I.N., Shchekina, M.P. & Anis’kov, A.A. Synthesis of Spiropyrrolidines and Spiropyrrolizidines from Azomethine Ylides. Chem Heterocycl Comp 50, 479–488 (2014). https://doi.org/10.1007/s10593-014-1498-z

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  • DOI: https://doi.org/10.1007/s10593-014-1498-z

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