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Synthesis 2017; 49(02): 299-309
DOI: 10.1055/s-0036-1588620
DOI: 10.1055/s-0036-1588620
paper
Multicomponent Diastereoselective Synthesis of Indolizidines via 1,3-Dipolar Cycloadditions of Azomethine Ylides
Further Information
Publication History
Received: 31 July 2016
Accepted after revision: 10 September 2016
Publication Date:
19 October 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201702/lookinside/thumbnails/ss-2016-t0541-op_10-1055_s-0036-1588620-1.jpg)
Dedicated to Professor Dieter Enders.
Abstract
The synthesis of polyfunctionalized indolizidines from pipecolinic acid alkyl ester derivatives, aldehydes and a wide range of dipolarophiles by multicomponent 1,3-dipolar cycloadditions is developed in a diastereoselective manner. The cycloadditions take place in toluene with short reaction times at 70 °C, giving good yields. The synthesis of these fused heterocycles is also studied starting from pipecolinic acid, generating the dipole through a decarboxylative route at 120 °C. The relative configuration of the resulting products as well as the mechanistic pathways are also explained.
Key words
cycloaddition - multicomponent - indolizidines - azomethine ylides - iminium route - decarboxylative routeSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588620.
- Supporting Information
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See for example:
See for example:
For general reviews dealing with 1,3-DC, see: