Diastereospecific cyclization of 3-arylidene-1-pyrrolinium salts containing an alkyltriarylphosphonium fragment: a path to the synthesis of new pyrrolizidine derivatives

Abstract

We report a diastereospecific method for the synthesis of phosphorus-containing pyrrolizidines based on the cyclization of 3-arylidene-1-pyrrolinium derivatives containing an alkyltriphenylphosphonium salt fragment catalyzed by sodium ethylate and water. A number of new phosphorus-containing pyrrolizidines were obtained with product yields reaching 99%. Experimental data were obtained, revealing the details of the mechanism of this reaction.

Graphical abstract: Diastereospecific cyclization of 3-arylidene-1-pyrrolinium salts containing an alkyltriarylphosphonium fragment: a path to the synthesis of new pyrrolizidine derivatives

Supplementary files

Article information

Article type
Paper
Submitted
19 Jun 2025
Accepted
27 Jul 2025
First published
08 Aug 2025

New J. Chem., 2025, Advance Article

Diastereospecific cyclization of 3-arylidene-1-pyrrolinium salts containing an alkyltriarylphosphonium fragment: a path to the synthesis of new pyrrolizidine derivatives

T. Rizbayeva, A. Smolobochkin, A. Gazizov, O. Babaeva, A. Lyubina, A. Sapunova, A. Voloshina, D. Gerasimova, A. Burilov and M. Pudovik, New J. Chem., 2025, Advance Article , DOI: 10.1039/D5NJ02552D

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