Diastereoselective synthesis of S-tert-butyl-beta-(trifluoromethyl)isocysteine.
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.
Ohkura
Hironari
H
Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan.
Handa
Michiharu
M
Katagiri
Toshimasa
T
Uneyama
Kenji
K
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
D002087:Butyrates; C462719:S-tert-butyl-beta-(trifluoromethyl)isocysteine; D008094:Lithium; D015032:Zinc; D003545:Cysteine