Optically active w-halo-2-aminoalkanecarboxylic acid...

C - Chemistry – Metallurgy – 07 – D

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C07D 263/18 (2006.01) C07F 9/30 (2006.01) C07F 9/653 (2006.01)

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CA 2075151

HOE 91/F 242 Abstract of the Disclosure Optically active .omega.-halo-2-aminoalkanecarboxylic acid derivatives, process for the preparation thereof and their use for the preparation of optically active phos- phorus-containing .alpha.-amino acids Optically active, cyclic (2S)- and (2R)-.omega.-halo-2- aminoalkanecarboxylic acid derivatives of the formula I and mixtures thereof, Image (I) in which R1is (C1-C6)alkyl which is unsubstituted or substituted by hydroxyl, alkoxyy, alkylcarbonyl and/or alkoxycarbonyl; or is alkenyl, alkynyl, R2-CO- or R3-SO2-, R2 is (C1-C11)alkyl, (substituted) (C6-C13)aryl, (C1- C6)alkoxy or (substituted) (C6-C13)aryl (C1-C6)alkoxy, R3 is (C1-C4)alkyl or (substituted) phenyl, X halogen and n is zero or one, are suitable starting materials for the preparation of a multiplicity of biologically active substances. They can be prepared by reaction of diacyl peroxides of the formula [R-CO-O-]2 in which R is defined as for the radical bound to X in the compounds I with a halogenation agent (for example halogens, PCl5) in the presence of a catalyst (for example CuCl). By means of a reaction of the Arbusov type with replacement of X by a (substituted) phosphinyl group, optically active intermediates can be obtained, which can be converted in a known manner into optically active phosphorus-containing amino acids such as L-phosphinothricin.

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