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

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

Molecules. 2017 Dec 4;22(12):2134. doi: 10.3390/molecules22122134.

Authors

Alexander Anis'kov¹, Irina Klochkova², Roman Tumskiy³, Alevtina Yegorova⁴

Affiliations

¹ Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia. aniskovalvis@gmail.com.
² Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia. v-klochkov1@yandex.ru.
³ Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia. roma_ronaldinho@rambler.ru.
⁴ Institute of Chemistry, Chernyshevsky Saratov State University, 83 Astrakhanskaya Street, Saratov 410012, Russia. yegorovaay@gmail.com.

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.

Keywords: 1,3-dipolar cycloaddition; azomethine ylides; sarcosine; spiro[indoline-3,2′-pyrrolidin]-2-one; unsaturated ketones.

MeSH terms

Cycloaddition Reaction
Cyclohexanones / chemistry*
Indoles / chemistry
Ketones / chemistry
Oxindoles
Pyrrolidines / chemistry*
Stereoisomerism

Substances

Cyclohexanones
Indoles
Ketones
Oxindoles
Pyrrolidines
2-oxindole
cyclohexanone