Diastereoselective Synthesis of Pyrrolidines via the Yb(OTf)3 Catalyzed Three-Component Reaction of Aldehydes, Amines, and 1,1-Cyclopropanediesters
- 25 August 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (20), 8242-8244
- https://doi.org/10.1021/jo0512251
Abstract
[Chemical reaction: see text] 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.Keywords
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