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Synthesis 2017; 49(13): 2819-2851
DOI: 10.1055/s-0036-1588423
DOI: 10.1055/s-0036-1588423
short review
Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine Ylides
Further Information
Publication History
Received: 23 January 2017
Accepted after revision: 02 April 2017
Publication Date:
07 June 2017 (online)
Dedicated to Prof. Ronald E. Grigg
Abstract
This review summarizes the trends in the formation of complex or not so complex heterocyclic structures through 1,3-dipolar cycloadditions of azomethine ylides. Diastereo- and enantioselective processes as well as non-asymmetric cycloadditions constitute very important synthetic tools for achieving these compounds. This review covers the literature from 2015 through 2016 and organizes the research in terms of biologically important heterocycles and natural products from cascade 1,3-dipolar cycloadditions of azomethine ylides to the simpler forms of 1,3-dipolar cycloaddition.
1 Introduction
2 Synthesis of Spirooxindoles
3 Synthesis of Spiropyrrolidines
4 Synthesis of Spiropiperidines and Piperidines
5 Synthesis of Pyrrolidines and Fused Pyrrolidines
6 Synthesis of Pyrrolizidines and Indolizidines
7 Synthesis of Quinolone and Isoquinolines
8 Conclusions
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Dispiroindole derivatives are known to have antidiabetic, anticancer, antitubercular, antibacterial as well as antimicrobial activities
Very similar work using a chiral ferrocenyl-oxazoline-phosphine ligand with an imidazolium unit was reported. The study of its recyclability was an interesting task:
For enantioselective 1,3-DC with alkylidenemalonates with these copper(II)·ligand catalysts: