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Sergey Tin, José A. Fuentes, Tomas Lebl and Matthew L. Clarke The Stability of Imidazolidinones is the Primary Influence on the Catalytic Activity of Proline Amides and Proline Sulfonamides in Enamine Catalysis Using Alkyl Aldehyde Substrates European Journal of Organic Chemistry 2013

Version of Record online: 9 NOV 2012 | DOI: 10.1002/ejoc.201201174

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Some proline amides are poor catalysts when aldehydes are used as substrates since the catalysts irreversibly form imidazolidinones. Proline amides with more basic amide groups form long-lived enamines, which allows catalysis to proceed. Proline sulfonamides only form imidazolidones, but these are unstable.

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