Soluble polymer supported synthesis of alpha-amino acid derivatives.
A Schiff base activated glycine supported on a soluble polymer (poly(ethylene glycol) (PEG)) was readily alkylated with a wide variety of electrophiles in the presence of a carbonate base in acetonitrile. The presence of the polymer provided a phase-transfer catalysis environment which accelerated the reaction. Effects of various carbonate bases and leaving groups have been also studied. Completion of the PEG-supported reaction was obtained without using a large excess of reagents or an extra phase-transfer catalyst, even in the case of unreactive or hindered electrophiles. After cleavage from the polymer, alpha-amino esters are obtained in good yields.
Sauvagnat
B
B
Laboratoire des Aminoacides, Peptides et Protéines, CNRS-Universités Montpellier 1 et 2, Montpellier, France.
Kulig
K
K
Lamaty
F
F
Lazaro
R
R
Martinez
J
J
D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis*; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D005998:Glycine / Q000737:chemistry; D011092:Polyethylene Glycols; D011108:Polymers; D011188:Potassium / Q000737:chemistry; D012545:Schiff Bases
D000596:Amino Acids; D002254:Carbonates; D011108:Polymers; D012545:Schiff Bases; D011092:Polyethylene Glycols; C037593:potassium carbonate; D011188:Potassium; D005998:Glycine