A practical route to fluoroalkyl- and fluoroarylamines by base-catalyzed [1,3]-proton shift reaction

The base-catalyzed [1,3]-proton shift reaction is shown to be an efficient general approach to fluoroalkyl and fluoroaryl amines starting from appropriate carbonyl compounds and benzylamine. The base-catalyzed [1,3]-proton shift reaction is shown to be a convenient general method for preparation of primary fluoroalkyl and fluoroaryl amines starting from appropriate carbonyl compounds and benzylamine

Transamination of fluorinated β-keto carboxylic esters. A biomimetic approach to β-polyfluoroalkyl-β-amino acids.

The base-catalyzed isomerization of N-benzylimines (or enamines) of β-polyfluoroalkyl-β-ketocarboxylic esters cleanly affords the N-benzylidene derivatives of β-polyfluoro-β-aminocarboxylic esters which are hydrolyzed to corresponding amino acids in high overall yields

Synthesis of optically pure (R)- and (S)-alpha-trifluoromethyl-alanine

+)-(R)- and (−)-(S)-3,3,3-trifluoro-2-methyl-alanine (1) were synthesized from (+)-(R)-methyl-p-tolyl-sulphoxide (5) and N-alkoxycarbonylimino derivatives 4 of methyl 3,3,3-trifluoropyruvate (3). The absolute configuration was determined by X-ray analyses of two synthetic intermediates (2S,RS)-6a and (2R,RS-6c

Chemo-enzymatic approach to the synthesis of each of the four isomers of α-alkyl-β-fluoroalkyl-substituted β-amino acids

Starting from easily available ethyl 2-methyl-4,4,4-trifluoroacetoacetate and benzylamine each of the four stereoisomers of α-methyl-β-trifluoromethyl-β-alanine have been synthesized in optically pure form via stereocontrolled chemo-enzymatic procedure including diastereoselective base-catalyzed [1,3]-proton shift reaction and enantioselective penicillin acylase-catalyzed resolution. Each of the four stereoisomers of α-methyl-β-trifluoromethyl-β-alanine have been synthesized via stereocontrolled chemo-enzymatic approach