O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids.
O-N Intramolecular alkoxycarbonyl (carbonate-carbamate) migration was found to occur as a common reaction of hydroxyamino acids under mild basic aqueous conditions with no formation of side products. Carbonate protective groups migrate to produce amino-protected carbamate derivatives of hydroxyamino acids with high efficiency and purity.
Skwarczynski
Mariusz
M
Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.
Sohma
Youhei
Y
Noguchi
Mayo
M
Kimura
Tooru
T
Hayashi
Yoshio
Y
Kiso
Yoshiaki
Y
D000596:Amino Acids / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D002219:Carbamates; D002254:Carbonates