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Grünenfelder CE, Kisunzu JK, Wennemers H. Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angew Chem Int Ed Engl. 2016;55(30):8571-4doi: 10.1002/anie.201602230.
Grünenfelder, C. E., Kisunzu, J. K., & Wennemers, H. (2016). Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angewandte Chemie (International ed. in English), 55(30), 8571-4. https://doi.org/10.1002/anie.201602230
Grünenfelder, Claudio E, et al. "Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide." Angewandte Chemie (International ed. in English) vol. 55,30 (2016): 8571-4. doi: https://doi.org/10.1002/anie.201602230
Grünenfelder CE, Kisunzu JK, Wennemers H. Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angew Chem Int Ed Engl. 2016 Jul 18;55(30):8571-4. doi: 10.1002/anie.201602230. Epub 2016 Jun 02. PMID: 27254460.
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Angew Chem Int Ed Engl. 2016 Jul 18;55(30):8571-4. doi: 10.1002/anie.201602230. Epub 2016 Jun 02.

Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide.

Angewandte Chemie (International ed. in English)

Claudio E Grünenfelder, Jessica K Kisunzu, Helma Wennemers

Affiliations

  1. Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
  2. Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland. [email protected].

PMID: 27254460 DOI: 10.1002/anie.201602230

Abstract

The tripeptide H-dPro-Pro-Asn-NH2 is presented as a catalyst for asymmetric conjugate addition reactions of aldehydes to maleimide. The peptidic catalyst promotes the reaction between various aldehydes and unprotected maleimide with high stereoselectivities and yields. The obtained products were readily derivatized to the corresponding pyrrolidines, lactams, lactones, and peptide-like compounds. (1) H NMR spectroscopic, crystallographic, and computational investigations provided insight into the conformational properties of H-dPro-Pro-Asn-NH2 and revealed the importance of hydrogen bonding between the peptide and maleimide for catalyzing the stereoselective C-C bond formation.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: addition reactions; asymmetric catalysis; maleimide; organocatalysis; peptides

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