Charlotte L. Barney

A convenient synthesis of hindered amines and α-trifluoromethylamines from ketones

Abstract Ketones and α-trifluoromethylketones were converted to primary, secondary, and tertiary amines in good to excellent yields by a reductive amination procedure utilizing TiCl 4 /NaCNBH 3 . The method provides the first direct route to α-trifluoromethylamines from ketones, and access to hindered amines from ketones which are unobtainable by Borch reducttve amination.

A new synthesis of 2-fluoro-1-olefins

Abstract The first examples of the addition of PhSeF to olefins to yield β-fluoro phenylselenides ( 2 ) are reported. β-Fluoro phenylselenides ( 2 ) obtained from terminal olefins were converted to the title vinyl fluorides 3 on treatment with ozone, whereas, 2 obtained from internal and cyclic olefins formed allyl fluorides. This method provides an entry to previously unreported 2-benzyl-2-fluoro-1-olefins (e.g. 3i ).

A convenient synthetic access to β,β-difluoro-γ-keto-α-amino acids. Application to the synthesis of a potential inhibitor of kynureninase

Abstract A convenient synthesis of a novel class of kynureninase inhibitors, difluoroketoamino acid ( 11 ) is described.

A facile synthesis of β-substituted-α-allenyl primary amines

Abstract Copper or nickel catalyzed substitution of Grignard reagents on the bis-trimethylsilyl protected 4-methoxy-2-butynylamine ( 2 ) provides β-substituted-α-allenyl primary amines ( 3 ) in high yield.

A convenient synthesis of erythro- and threo-3-fluorophenyl- alanine from a protected glycine synthon

A facile synthesis of the title compounds (8 and 9) is described; key steps include the mono-C-alkylation of the glycine Schiff base benzyl ester 1a with α-bromo-α-fluorotoluene, which provides the readily separable fluorinated diastereomers 2a and 3a, and the dealkylative hydrolysis of the benzyl esters 2a-5a without concomitant loss of the benzylic fluorine.

The synthesis of N-substituted tetrahydropyridines using the hetero-cope rearrangement

Abstract Several imines have been prepared from methacrolein dimer. Thermal rearrangement of these molecules resulted in the formation of N-substituted tetrahydropyridines.

New pathway for the reaction of difluorocarbene with imines

The reaction of chlorodifluoromethane with the benzophenone Schiff base of ethyl glycinate (1) provided the novel ethyl 1-difluoromethyl-2,2-diphenylaziridine-3-carboxylate (2), the crystal structure of which has been determined.