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Diastereoselective Synthesis of Pyrrolidines via the Yb(OTf)₃ Catalyzed Three-Component Reaction of Aldehydes, Amines, and 1,1-Cyclopropanediesters

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Cheryl A. Carson and Michael A. Kerr*

Department of Chemistry, The University of Western Ontario, London, Ontario, Canada, N6A 5B7 makerr@uwo.ca

J. Org. Chem., 2005, 70 (20), pp 8242–8244

DOI: 10.1021/jo0512251

Publication Date (Web): August 25, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Aldimines, generated in situ by the reaction of primary amines or anilines with aldehydes, undergo smooth reaction with various 1,1-cyclopropanediesters in the presence of catalytic Yb(OTf)₃. The products are pyrrolidines in which the major diastereomer bears a cis relationship between substituents at the 2- and 5-positions. In most cases the diastereoselectivity is greater than 10:1.

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Published In Issue September 30, 2005
Received June 15, 2005

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Diastereoselective Synthesis of Pyrrolidines via the Yb(OTf)₃ Catalyzed Three-Component Reaction of Aldehydes, Amines, and 1,1-Cyclopropanediesters