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Synthesis 2009(20): 3443-3448  
DOI: 10.1055/s-0029-1216970
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Cerium(III) Chloride Heptahydrate-Lithium Iodide: A Novel Reagent System for the Synthesis of N-Arylpyrrolidines

J. S. Yadav*, B. V. Subba Reddy, G. Narasimhulu, D. Chandrakanth, G. Satheesh
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27193535; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 25 May 2009
Publication Date:
28 August 2009 (online)

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Abstract

Aldimines, generated in situ from arylamines and aryl aldehydes, undergo smooth cycloaddition with cyclopropane-1,1-dicarboxylate in the presence of the cerium(III) chloride heptahydrate-lithium iodide reagent system in refluxing acetonitrile under neutral conditions to produce the corresponding N-arylpyrrolidines in good yields with high selectivity.

Key words

cerium(III) reagents - aldimines - cyclopropanedicarboxylate - pyrrolidines - cycloadditions - ring expansion

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