A method for cleaving an allyl protecting group at the amide nitrogen of peptides by one-pot olefin isomerization-oxidation.
A facile method for N-deallylation at the amide nitrogen of peptides is described. One-pot deallylation of a substrate through ruthenium hydride-catalyzed terminal olefin isomerization and subsequent ozonolysis gave the corresponding deallylated product under mild conditions.
Kajihara
Kouki
K
Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo 060-0812 Japan.
Arisawa
Mitsuhiro
M
Shuto
Satoshi
S
D000475:Alkenes / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D015195:Drug Design; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D010126:Ozone; D010455:Peptides / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
D000475:Alkenes; D000577:Amides; D010455:Peptides; D010126:Ozone; D012428:Ruthenium; D009584:Nitrogen; D010100:Oxygen