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Molecules 2017, 22(12), 2134; doi:10.3390/molecules22122134

A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition

Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia
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Received: 30 September 2017 / Revised: 29 November 2017 / Accepted: 2 December 2017 / Published: 4 December 2017
(This article belongs to the Special Issue Advances in Spiro Compounds)
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Abstract

For the first time, arylmethylidene cyclohexanones that are non-symmetrical due to the presence of peripheral substituents were studied in 1,3-dipolar cycloaddition reactions. It is shown that the interaction with the azomethine ylide generated from sarcosine proceeds regio- and diastereoselectively, with the participation of two non-equivalent parts of the dipolarophile. Also for the first time, β-amino ketones (Mannich bases) were used as dipolarophile equivalents of unsaturated ketones. It was found that cycloaddition occurs diastereoselectively at the generated center. View Full-Text
Keywords: spiro[indoline-3,2′-pyrrolidin]-2-one; azomethine ylides; unsaturated ketones; 1,3-dipolar cycloaddition; sarcosine spiro[indoline-3,2′-pyrrolidin]-2-one; azomethine ylides; unsaturated ketones; 1,3-dipolar cycloaddition; sarcosine
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Anis’kov, A.; Klochkova, I.; Tumskiy, R.; Yegorova, A. A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition. Molecules 2017, 22, 2134.

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