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Synthesis 2016; 48(07): 1055-1068
DOI: 10.1055/s-0035-1561331
DOI: 10.1055/s-0035-1561331
paper
2-Formylpyrroles as Building Blocks in a Divergent Synthesis of Pyrrolizines
Further Information
Publication History
Received: 13 November 2015
Accepted after revision: 31 December 2015
Publication Date:
28 January 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201607/lookinside/thumbnails/ss-2015-m0659-op_10-1055_s-0035-1561331-1.jpg)
Abstract
The selective functionalization of 2-formylpyrrole to provide diverse 1,2- and 1,2,5-substituted pyrroles is described. These compounds were used as versatile building blocks in a divergent synthesis of biologically valuable aza-bycyclic skeletons, such as pyrrolizine and pyrrolizidine derivatives. These bicycles were prepared following metal-free cascade synthetic approaches via regioselective intramolecular 1,3-dipolar cycloadditions and stereoselective Knoevenagel/Michael/ cyclization with dimethyl malonate.
Key words
2-formylpyrrole - pyrrolizines - pyrrolizidines - cascade reactions - Knoevenagel/Michael/cyclizationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561331.
- Supporting Information
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