title: Diastereoselective synthesis of S-tert-butyl-beta-(trifluoromethyl)isocysteine.
abstract: Both diastereoisomers of S-tert-butyl-beta-(trifluoromethyl)isocysteine have been synthesized stereoselectively by the sequential reactions of trifluoroacetimidoyl chloride with the lithium enolate of tert-butyl alpha-tert-butylthioacetate, followed by the diastereoselective reduction of the imino group with sodium borohydride in the presence of zinc(II) or di(ethylene glycol) dimethyl ether, and finally by the deprotection of N-aryl and tert-butyl ester groups.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan.
authors.forename: Hironari
authors.initials: H
authors.lastname: Ohkura
authors.forename: Michiharu
authors.initials: M
authors.lastname: Handa
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Katagiri
authors.forename: Kenji
authors.initials: K
authors.lastname: Uneyama
mesh_terms: D002087:Butyrates / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D018360:Crystallography, X-Ray; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D002087:Butyrates; C462719:S-tert-butyl-beta-(trifluoromethyl)isocysteine; D008094:Lithium; D015032:Zinc; D003545:Cysteine