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Synlett 2012(4): 585-588  
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

Hongxiang Xie, Jinbao Xiang, Qun Dang*, Xu Bai*
The Center for Combinatorial Chemistry and Drug Discovery, The College of Chemistry and The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. of China
Fax: +86(431)85188900; e-Mail: xbai@jlu.edu.cn; e-Mail: qdang@jlu.edu.cn;
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Publication History

Received 26 October 2011
Publication Date:
06 February 2012 (online)

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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

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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.