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Synthesis 2012; 44(13): 1983-1992
DOI: 10.1055/s-0031-1290969
DOI: 10.1055/s-0031-1290969
paper
Diastereocontrol in the Synthesis of 2,3,4-Trisubstituted Pyrrolidines and Tetrahydrofurans via a Palladium(II)-Catalyzed Three-Component Coupling Reaction
Further Information
Publication History
Received: 31 January 2012
Accepted after revision: 23 March 2012
Publication Date:
05 June 2012 (online)
Abstract
The synthesis of trisubstituted pyrrolidines and tetrahydrofurans from boronic acids, allenes, and imines or aldehydes via a five- and a three-step protocol, respectively, is described. The assignment of the relative stereochemistry in the pyrrolidines and tetrahydrofurans confirmed the mechanistically significant stereochemical divergence of the palladium-catalyzed three-component coupling reaction. The methodology is applicable to the preparation of combinatorial libraries of pyrrolidines related to pharmaceutical agents and bioactive natural products.
Key words
stereoselective synthesis - heterocycles - palladium - multicomponent reactions - ring closureSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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