Direct asymmetric intramolecular alkylation of beta-alkoxy-alpha-amino esters via memory of chirality.
The intramolecular alpha-alkylation of beta-alkoxy-alpha-amino esters derived from L-serine proceeded predominantly over beta-elimination. When beta-alkoxy-alpha-amino esters were treated with powdered CsOH in DMSO at 20 degrees C, alpha-alkoxymethyl cyclic amino esters were obtained in up to 94% ee. Optically active THF amino acids were synthesized for the first time by the present method.
Moriyama
Katsuhiko
K
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Sakai
Hiroki
H
Kawabata
Takeo
T
D000478:Alkylation; D000598:Amino Acids, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
D000598:Amino Acids, Cyclic; D004952:Esters; D012694:Serine