- Biomimetic transamination of α-keto perfluorocarboxylic esters. An efficient preparative synthesis of β,β,β-trifluoroalanine
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An efficient large-scale preparative synthesis of biologically interesting β,β,β-trifluoroalanine through the biomimetic transamination of the ethyl trifluoropyruvate has been developed. The azomethine-azomethine isomerization of the N-(1-phenyl)ethylimine of ethyl trifluoropyruvate to the N-(l-phenyl)ethylidene alanine ethyl ester, a key stage of the process, was found to occur under the mild reaction conditions, in a triethylamine solution at rt. The proposed working mechanistic rationale accounting for the easiness of the isomerization and its stereochemical outcome, involves unusual non-asymmetric [1,5]-proton shift transfer from the methine carbon to the enolate oxygen.
- Soloshonok, Vadim A.,Kukhar, Valery P.
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p. 8307 - 8314
(2007/10/03)
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- New Synthetic Pathways to 3,3,3-Trifluoroalanine, 2-Deutero-3,3,3-trifluoroalanine and their Derivatives
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New synthetic pathways to 3,3,3-trifluoroalanine, 2-deutero-3,3,3-trifluoroalanine, their esters, amides, and thioamides are described, starting from hexafluoroacetone, and trifluoropyruvates, respectively.
- Burger, Klaus,Hoess, Eva,Gaa, Karl,Sewald, Norbert,Schierlinger, Christian
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p. 361 - 384
(2007/10/02)
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