Biomimetic transamination of α-keto perfluorocarboxylic esters. An efficient preparative synthesis of β,β,β-trifluoroalanine

Add time:07/25/2019    Source:sciencedirect.com

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-(1-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.

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