Asymmetric fluorine-containing primary amines and their preparat

Details Asymmetric fluorine-containing primary amines and their preparat Asymmetric fluorine-containing primary amines and their preparat

1997-12-17

1999-08-17

Barts, Samuel

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564470, 564471, C07C21100

Patent

active

059395885

ABSTRACT:
The present invention, which is aimed at providing a novel reaction for converting a fluorine-containing carbonyl compound to an asymmetric fluorine-containing primary amine, relates to a method in which a Schiff base obtained by the condensation of a fluorine-containing carbonyl compound and an asymmetric amine ((S)- or (R)-1-phenylethylamine) is treated in the presence of an appropriate organic base to hydrolyze a tautomeric imine obtained by asymmetrically performing an enzyme-like transamination reaction, yielding an asymmetric fluorine-containing amine.

REFERENCES:
W.R. Nes, et al., J. Am. Soc., vol. 72, pp. 5409-5413, Dec. 1950, "Amine and Enol Derivatives of 1,1,1-Trifluoropropane.sup.1 ".
Vadim A. Soloshonok, et al., "A Practical Route to Fluoroalkyl-and Tetrahedron Letters, vol. 35, No. 19, (1994), pp. 3119-3122. Reaction. A Practical Synthesis of .beta.-Fluoroalkyl-.beta.-Amino Acids," Tetrahedron, vol. 52, No. 20, (1996), pp. 6953-6964.
Vadim A. Soloshonok, et al., "The Effect of Substituents on the Feasibility of Azomethine-Azomethine Isomerization: New Synthetic Opportunities for Biomimetic Transamination," Tetrahedron, vol. 52, No. 47, (1996), pp. 14701-14712.
Vadim A. Soloshonok, et al., "The Effect of Substituents on the Feasibility 9, (Sep., 1996), pp. 919-921.
Taizo Ono, et al., "Biomimetic Reductive Amination of Fluoro Aldehydes and Journal of Organic Chemistry, vol. 61, No. 19, (1996), pp. 6563-6569.
Vadim A. Soloshonok, et al., "Catalytic Asymmetric Synthesis of Reaction," Tetrahedron Letters, vol. 35, No. 28, (1994), pp. 5063-5064.

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