title: Enantioselective synthetic method for alpha-alkylserine via phase-transfer catalytic alkylation of 2-phenyl-2-oxazoline-4- carbonylcamphorsultam.
abstract: [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.
authors.affiliation: Research Institute of Pharmaceutical Science and College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
authors.forename: Jihye
authors.initials: J
authors.lastname: Lee
authors.forename: Yeon-Im
authors.initials: YI
authors.lastname: Lee
authors.forename: Myoung Joo
authors.initials: MJ
authors.lastname: Kang
authors.forename: Yeon-Ju
authors.initials: YJ
authors.lastname: Lee
authors.forename: Byeong-Seon
authors.initials: BS
authors.lastname: Jeong
authors.forename: Jeong-Hee
authors.initials: JH
authors.lastname: Lee
authors.forename: Mi-Jeong
authors.initials: MJ
authors.lastname: Kim
authors.forename: Ji-yeon
authors.initials: JY
authors.lastname: Choi
authors.forename: Jin-Mo
authors.initials: JM
authors.lastname: Ku
authors.forename: Hyeung-geun
authors.initials: HG
authors.lastname: Park
authors.forename: Sang-sup
authors.initials: SS
authors.lastname: Jew
mesh_terms: 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
chemical_list: 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