Increased Structural Complexity Leads to Higher Activity: Peptides as Efficient and Versatile Catalysts for Asymmetric Aldol Reactions

Philipp Krattiger, Roman Kovasy, Jefferson D. Revell, Stanislav Ivan and Helma Wennemers*

*Department of Chemistry, University of Basel, St. Johanns Ring 19, CH-4056 Basel, Switzerland, Email: helma.wennemersunibas.ch

P. Krattiger, R. Kovasy, J. D. Revell, S. Ivan, H. Wennemers, Org. Lett., 2005, 7, 1101-1103.

DOI: 10.1021/ol0500259 (free Supporting Information)

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Abstract

H-Pro-Pro-Asp-NH₂ and H-Pro-D-Ala-D-Asp-NH₂ have been identified as catalytically active peptides for aldol reactions within a 3375-membered split-and-mix library using the method of "catalyst-substrate coimmobilisation". The two selected peptides are highly efficient catalysts for asymmetric aldol reactions offering an activity that is considerably higher compared to that of proline.

The paper demonstrates that slightly higher complexity can be a good trade-off for higher activity and presents a general concept for the identification of catalysts which are difficult to design rationally.

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Key Words

Aldol Reaction, Aldol Addition, Organocatalysis

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ID: J54-Y2005-290