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Aniskov A. A., Klochkova I. ., Schekina M. P., Andreev K. A., Tumskiy R. S. Stereochemical Aspects of Reaction of 1,3-dipolar Cycloaddition in a Row of Conjugated Enones. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2016, vol. 16, iss. 1, pp. 35-42. DOI:

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Stereochemical Aspects of Reaction of 1,3-dipolar Cycloaddition in a Row of Conjugated Enones


The reaction of 1,3-dipolar cycloaddition of conjugated aryl(hetaryl) methylideneacetones, which containing various peripheral substituents, with azomethine ylides was carried out. It was established that the interaction is not chemoselective and proceeds with the participation of two non-equivalent reaction centers of dipolarophile with high diastereoselectivity. The products of cycloaddition were a mixture of structural isomers endo-cycloaddition. Monoenone transform to spyropyrrolidines with high endo-stereoselectivity.


1. Arumugam N., Periyasami G., Raghunathan R., Kamalraj S., Muthumary J. Synthesis and antimicrobial activity of highly functionalised novel β-lactam grafted spiropyrrolidines and pyrrolizidines // Eur. J. Med. Chem. 2011. Vol. 46, iss. 2. P. 600–608.

2. Prasanna R., Purushothaman S., Raghunathan R. Highly regioselective synthesis of glycospiro heterocycles through 1,3-dipolar cycloaddition reaction // Tetrahedron Lett. 2010. Vol. 51, iss. 11. P. 4538–4544.

3. Pellissier Н. Asymmetric 1,3-dipolar cycloadditions // Tetrahedron. 2007. Vol. 63, iss. 7. P. 3235–3243. 

4. Kumar R. R., Perumal S. A facile synthesis and highly atom economic 1,3-dipolar cycloaddition of hexahydropyrido[3,4-c][1,5]benzothiazepines with nitrile oxide: stereoselective formation of hexahydro [1,2,4]oxadiazolo[5,4-d]pyrido[3,4-c][1,5]benzothiazepines // Tetrahedron. 2007. Vol. 63, iss. 4. P. 7850–7858.

5. Sridhar G., Gunasundari T., Raghunathan R. A greener approach for the synthesis of 1-N-methyl-(spiro[2.3′]oxindolespiro[3.2″]/spiro[2.3′]indan-1,3-dionespiro[2.2″]) cyclopentanone-4-aryl pyrrolidines // Tetrahedron Lett. 2007. Vol. 48. P. 319–326.

6. Lakshmi N. V., Thirumurugan P., Perumal P. T. An expedient approach for the synthesis of dispiropyrrolidine bisoxindoles, spiropyrrolidine oxindoles and spiroindane-1,3-diones through 1,3-dipolar cycloaddition reactions // Tetrahedron Lett. 2010. Vol. 51. P. 1064.

7. Клочкова И. Н., Аниськов А. А., Щекина М. П. Первый пример взаимодействия несимметричных диенонов с 1,3-диполем. Синтез спиропирролидинов // ХГС. 2011. Т. 47, вып. 9. С. 1425–1433.

8. Клочкова И. Н., Аниськов А. А., Щекина М. П. Синтез спиропирролидинов и спиропирролизидинов на основе азометин-илидов // ХГС. 2014. Т. 50, вып. 4. С. 527–536.

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