PROCESS FOR PRODUCING OPTICALLY ACTIVE OMEGA-HALOGEN-2-AMINO-ALKANECARBOXYLIC ACID DERIVATIVES AND OPTICALLY ACTIVE PHOSPHOROUS ALPHA-AMINO ACIDS BY USING SUCH DERIVATIVES

摘要

Optically active, cyclic (2S)- and (2R)-l-halo-2-amino- alkanecarboxylic acid derivatives of the formula I and their mixtures IMAGE in which R1 denotes (C1-C6)alkyl which is unsubstituted or substituted by hydroxyl, alkoxy, alkylcarbonyl and/or alkoxycarbonyl, or denotes alkenyl, alkynyl, R2-CO- or R3-SO2-, R2 denotes (C1-C11)alkyl, (subst.) (C6-C13)aryl, (C1-C6)alkoxy or (subst.) (C6-C13)aryl-(C1-C6)alkoxy, R3 denotes (C1-C4)alkyl or (subst.) phenyl, X denotes halogen and n denotes zero or one, are suitable as starting substances 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 the radical bonded to X in the compounds I, with a halogenating agent (e.g. halogens, PCl5) in the presence of a catalyst (e.g. CuCl). By a reaction of the Arbusov type with replacement of X by a (subst.) 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.