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Synfacts 2010(1): 0027-0027  
DOI: 10.1055/s-0029-1218468
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Cerium(III)-Catalyzed Synthesis of N-Arylpyrrolidines

Contributor(s): Victor Snieckus, Timothy Hurst
J. S. Yadav*, B. V. S. Reddy, G. Narasimhulu, D. Chandrakanth, G. Satheesh
Indian Institute of Chemical Technology, Hyderabad, India
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

A simple and efficient 3-component coupling of arylamines 1, benzaldehydes 2, and diethyl cyclopropane-1,1-dicarboxylate (3) to afford N-arylpyrrolidines 4 is reported. The reaction proceeds under relatively mild conditions and in excellent yield. This process is tolerant of wide-ranging functionality including EDG and EWG on both the amine and aldehyde fragments. Disappointingly, attempts to extend the scope to aliphatic substrates proved unsuccessful under these conditions.