Highly enantioselective synthesis of (R)-alpha-alkylserines via phase-transfer catalytic alkylation of o-biphenyl-2-oxazoline-4-carboxylic acid tert-butyl ester using cinchona-derived catalysts.
[reaction: see text] A highly enantioselective synthetic method for (R)-alpha-alkylserines was developed by the phase-transfer catalytic alkylation of o-biphenyl-2-oxazoline-4-carboxylic acid tert-butyl ester (4i) using cinchona-derived phase-transfer catalyst N(1)-(9-anthracenylmethyl)-O(9)-allyl-dihydrocinchonidinium bromide (up to 96% ee).
Lee
Yeon-Ju
YJ
Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Lee
Jihye
J
Kim
Mi-Jeong
MJ
Kim
Taek-Soo
TS
Park
Hyeung-Geun
HG
Jew
Sang-Sup
SS
D000475:Alkenes / Q000138:chemical synthesis*; D000478:Alkylation; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D002929:Cinchona / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D002264:Carboxylic Acids; D010080:Oxazoles; D012694:Serine