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