Enantioselective synthetic method for alpha-alkylserine via phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4- carbonylcamphorsultam.
[reaction: see text] An enantioselective synthetic method for alpha-alkylserines by the phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4-carbonylcamphorsultam (4a) was developed. The phase-transfer catalytic alpha-alkylation of 4a using P2-Et at -78 degrees C gave alpha-alkylation (75 to approximately 99%, 90 to approximately 97% de), which could be easily hydrolyzed to alpha-alkylserines.
Lee
Jihye
J
Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Lee
Yeon-Im
YI
Kang
Myoung Joo
MJ
Lee
Yeon-Ju
YJ
Jeong
Byeong-Seon
BS
Lee
Jeong-Hee
JH
Kim
Mi-Jeong
MJ
Choi
Ji-yeon
JY
Ku
Jin-Mo
JM
Park
Hyeung-geun
HG
Jew
Sang-sup
SS
D000478:Alkylation; D002264:Carboxylic Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005054:Eugenol / Q000031:analogs & derivatives* / Q000737:chemistry*; D008956:Models, Chemical; D010080:Oxazoles / Q000737:chemistry*; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
C503011:2-phenyl-2-oxazoline-4- carbonylcamphorsultam; C488313:2-phenyl-2-oxazoline-4-carboxylic acid tert-butyl ester; D002264:Carboxylic Acids; D004952:Esters; D010080:Oxazoles; D005054:Eugenol; D012694:Serine