Highly enantioselective synthesis of (S)-alpha-alkyl-alpha,beta-diaminopropionic acids via asymmetric phase-transfer catalytic alkylation of 2-phenyl-2-imidazoline-4-carboxylic acid tert-butyl esters.
An efficient enantioselective synthetic method for (S)-alpha-alkyl-alpha,beta-diaminopropionic acid is reported. The asymmetric phase-transfer catalytic alkylation of N(1)-Boc-2-phenyl-2-imidazoline-4-carboxylic acid tert -butyl ester in the presence of chiral quaternary ammonium catalyst gave the corresponding alkylated products (93-98% ee) which could be transformed to enantioenriched alpha-alkyl-alpha,beta-diaminopropionic acids.
Park
Yohan
Y
Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Kang
Sukhoon
S
Lee
Young Ju
YJ
Kim
Taek-Soo
TS
Jeong
Byeong-Seon
BS
Park
Hyeung-geun
HG
Jew
Sang-sup
SS
D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D015091:beta-Alanine; C011757:2,3-diaminopropionic acid