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Synlett 2012(4): 585-588
DOI: 10.1055/s-0031-1290333
DOI: 10.1055/s-0031-1290333
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Highly Stereocontrolled Intramolecular Cycloaddition Reaction of Azomethine Ylide Activated by a Pyrimidine Ring: Access to Novel Tricyclic Hexahydro-1H-pyrrolo[2′,3′:4,5]pyrido[2,3-d]pyrimidines
Further Information
Received
26 October 2011
Publication Date:
06 February 2012 (online)
Publication History
Publication Date:
06 February 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201204/lookinside/thumbnails/10.1055-s-0031-1290333-1.jpg)
Abstract
A pyrimidine ring was discovered to aid formation of an azomethine ylide undergoing intramolecular cycloaddition reactions. This method enabled efficient synthesis of a novel tricyclic pyrimidine-piperidine-pyrrolidine scaffold from various pyrimidinemethyl amines and aldehydes in complete stereocontrol and could be rationalized by an S-shaped azomethine ylide intermediate.
Key words
azomethine ylide - intramolecular cycloaddition - 1,3-dipolar cycloaddition - pyrimidine - pyrrolidine
- Supporting Information for this article is available online:
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References and Notes
CCDC 848492 (11a), CCDC 848493 (11q) and CCDC 848494 (11v) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.