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

Alexander Anis’kov; Irina Klochkova; Roman Tumskiy; Alevtina Yegorova

doi:10.3390/molecules22122134

Molecules (Dec 2017)

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

Alexander Anis’kov,
Irina Klochkova,
Roman Tumskiy,
Alevtina Yegorova

Affiliations

Alexander Anis’kov: Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia
Irina Klochkova: Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia
Roman Tumskiy: Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia
Alevtina Yegorova: Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia

DOI: https://doi.org/10.3390/molecules22122134
Journal volume & issue: Vol. 22, no. 12
p. 2134

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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