Diastereoselective synthesis of S-tert-butyl-beta-(trifluoromethyl)isocysteine.

Autor: Ohkura H; Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan., Handa M, Katagiri T, Uneyama K
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2002 Apr 19; Vol. 67 (8), pp. 2692-5.
DOI: 10.1021/jo016108u
Abstrakt: 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.
Databáze: MEDLINE