A straightforward approach towards glycoamino acids and glycopeptides via Pd-catalysed allylic alkylation.
Chelated enolates are versatile nucleophiles for palladium-catalysed allylic alkylations. Even with complex allylic substrates the reaction proceed without significant isomerisation. This allows the stereoselective introduction of polyhydroxylated allylic sidechains into amino acids and peptides with retention of the olefin geometry.
Krämer
Katja
K
Institut für Organische Chemie, Universität des Saarlandes, D-66123, Saarbrücken, Germany. u.kazmaier@mx.uni-saarland.de
Deska
Jan
J
Hebach
Christina
C
Kazmaier
Uli
U
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D002621:Chemistry / Q000379:methods*; D015195:Drug Design; D006020:Glycopeptides / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry; D013237:Stereoisomerism; D013912:Threonine / Q000737:chemistry
D000596:Amino Acids; D006020:Glycopeptides; D006027:Glycosides; D008024:Ligands; D010455:Peptides; D013912:Threonine; D010165:Palladium