title: Peptide-catalyzed 1,4-addition reactions of aldehydes to nitroolefins.
abstract: Conjugate addition reactions of aldehydes to nitroolefins provide synthetically useful gamma-nitroaldehydes. Here we summarize our research on peptide-catalyzed conjugate addition reactions of aldehydes to differently substituted nitroolefins. We show that peptides of the general type Pro-Pro-Xaa (Xaa = acidic amino acid) are not only highly active, robust and stereoselective catalysts but have also remarkable chemoselectivities.
authors: ETH Zürich, Laboratorium für Organische Chemie, Wolfgang-Pauli-Str. 10, CH-8093 Zürich.
authors: Robert
authors: R
authors: Kastl
authors: Yukihiro
authors: Y
authors: Arakawa
authors: Jörg
authors: J
authors: Duschmalé
authors: Markus
authors: M
authors: Wiesner
authors: Helma
authors: H
authors: Wennemers
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004151:Dipeptides / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D010446:Peptide Fragments / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D004151:Dipeptides; D009574:Nitro Compounds; D010446:Peptide Fragments; C448039:prolyl-proline