Cite this article as:

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: https://doi.org/10.18500/1816-9775-2016-16-1-35-42

This is an open access article distributed under the terms of Creative Commons Attribution 4.0 International License (CC-BY 4.0).
Heading: 
Chemistry
UDC: 
547.812’497.1
Language: 
Russian

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

Authors: 
Aniskov Alexandr Andreevich, SSU. Institute of Chemistry. Department of Organic and Bioorganic Chemistry, 410012, Saratov, Astrakhanskaya str., 83, building. 1, Institute of Chemistry, SSU, sch.mary@mail.ru
Klochkova Iraida Nikolaevna, SSU. Institute of Chemistry. Department of Organic and Bioorganic Chemistry, 410012, Saratov, Astrakhanskaya str., 83, building. 1, Institute of Chemistry, SSU, sch.mary@mail.ru
Schekina Marya Pavlovna, SSU. Institute of Chemistry., 410012, Saratov, Astrakhanskaya str., 83, building. 1, Institute of Chemistry, SSU, sch.mary@mail.ru
Andreev Kirill Alexandrovich, SSU. Institute of Chemistry. Department of Organic and Bioorganic Chemistry, 410012, Saratov, Astrakhanskaya str., 83, building. 1, Institute of Chemistry, SSU, andreevkachem@yandex.ru
Tumskiy Roman Sergeevich, Saratov State University , 83, Astrakhanskaya str., Saratov, 410012, Russia , rome.ru@yandex.ru
Abstract

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.

Key words: 
1, 3-dipolar cycloaddition, unsaturated ketones, azomethine ylides
DOI: 
https://doi.org/10.18500/1816-9775-2016-16-1-35-42
References

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