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Synthesis 2024; 56(15): 2432-2444
DOI: 10.1055/s-0040-1720114
DOI: 10.1055/s-0040-1720114
paper
A Novel Methodology for the Asymmetric Synthesis of 2,3,5-Trisubstituted Piperazine Derivatives
We thank the Scientific and Technological Research Council of Turkey (Türkiye Bilimsel ve Teknolojik Araştırma Kurumu; TUBITAK, Grant No. 221Z173) and the Middle East Technical University (METU; Orta Doğu Teknik Üniversitesi) for financial support.
Abstract
Piperazines constitute an important structural feature of many pharmaceuticals. For the discovery of new drugs, the ability to modify the lead compound’s structure is crucial. Herein, we provide an efficient method for the synthesis of chiral 2,3,5-trisubstituted piperazine structures. Our route enables the synthesis of several novel chiral aryl aziridinyl ketones that could be converted into aziridine-fused bicyclic imines. The reduction of these imines and the nucleophilic ring-opening reaction of the aziridine ring allowed us to synthesize highly functionalized piperazine derivatives.
Key words
piperazines - asymmetric synthesis - aziridines - Staudinger reaction - intramolecular cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720114.
- Supporting Information
Publication History
Received: 19 February 2024
Accepted after revision: 26 March 2024
Article published online:
10 April 2024
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