title: Selective peptide modifications via ruthenium-catalyzed allylic alkylations.
abstract: Ruthenium-catalyzed allylic alkylations are an interesting alternative to palladium-catalyzed processes, since they can provide products which are not accessible under Pd-catalysis. Chiral terminal allylic substrates can be reacted with perfect stereo- and regioretention, and also (Z)-configured allylic substrates can be converted isomerization-free. This allows highly stereoselective modifications of peptides at glycine subunits. The configuration at the α-position of the new generated α-amino acid can be controlled by the chiral peptide chain, and at the β-position by using chiral allylic substrates.
authors.affiliation: Universität des Saarlandes, Institut für Organische Chemie , Campus, Geb. C4.2, D-66123 Saarbrücken, Germany.
authors.forename: Anton
authors.initials: A
authors.lastname: Bayer
authors.forename: Uli
authors.initials: U
authors.lastname: Kazmaier
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000596:Amino Acids; D010455:Peptides; D010165:Palladium; D012428:Ruthenium