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Synthesis 2010(9): 1568-1571  
DOI: 10.1055/s-0029-1218651
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Peptide-Catalyzed Conjugate Addition Reactions of Aldehydes to Nitroolefins

Markus Wiesner, Helma Wennemers*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
Fax: +41(61)2670976; e-Mail: Helma.Wennemers@unibas.ch;
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Publikationsverlauf

Received 21 December 2009
Publikationsdatum:
25. Januar 2010 (online)

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Abstract

The tripeptide H-d-Pro-Pro-Glu-NH2 is an efficient catalyst for conjugate addition reactions of aldehydes to nitroolefins. Chiral γ-nitroaldehydes are obtained in excellent yields and stereoselectivities in the presence of as little as 1 mol% of the tripeptide catalyst. Under further optimized reaction conditions the product was obtained in essentially perfect stereoselectivity (syn/anti, >99:1, 99% ee).

Key words

asymmetric catalysis - conjugate addition reactions - organocatalysis - peptides - proline

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9

For the role of water and its effect on the reaction rate see ref. 8.