Process for Preparing Chiral 3-Triazolyl Sulphoxide Derivatives

1 . Process for preparing 3-triazolyl sulphoxide derivatives of the formula (I) in an enantiomerically pure or enantiomerically enriched form

in which

X 1 and X 2 are each independently fluorine, chlorine, bromine, hydrogen, (C 1 -C 12 )alkyl, (C 1 -C 12 )haloalkyl,

Y 1 and Y 2 are each independently fluorine, chlorine, bromine, hydrogen, (C 1 -C 12 )alkyl, (C 1 -C 12 )haloalkyl,

R 1 and R 2 are each independently hydrogen, (C 1 -C 12 )alkyl, (C 1 -C 12 )haloalkyl, cyano, halogen, nitro,

R 3 is hydrogen, (C 1 -C 12 )alkyl, amino, nitro, NH(CO)(C 1 -C 12 )alkyl, N═CR′R

where R, R′ are each independently hydrogen, (C 1 -C 12 )alkyl, aryl,

characterized in that

(A) a sulphide of the formula (II)

in which X 1 , X 2 , Y 1 , Y 2 , R 1 , R 2 and R 3 are each as defined above

is converted in the presence of a chiral catalyst and of an oxidizing agent.

2 . Process according to claim 1 , characterized in that the enantiomer ratio is 50.5:49.5 to 99.5:0.5 (+):(−) or (−):(+)-enantiomer.

3 . Process according to either of claims 1 and 2 , characterized in that the enantiomer ratio is 50.5:49.5 to 99.5:0.5 (+):(−) enantiomer.

4 . Process according to any of claims 1 to 3 , characterized in that

X 1 and X 2 , Y 1 and Y 2 are each independently fluorine, chlorine, hydrogen, (C 1 -C 12 )haloalkyl,

R 1 and R 2 are each independently fluorine, hydrogen, (C 1 -C 6 )alkyl,

R 3 is hydrogen, amino.

5 . Process according to any of claims 1 to 4 , characterized in that

X 1 and X 2 , Y 1 and Y 2 are each independently fluorine, hydrogen, (C 1 -C 6 )haloalkyl,

R 1 and R 2 are each independently fluorine, methyl,

R 3 is hydrogen.

6 . Process according to any of claims 1 to 5 , characterized in that the oxidizing agents used are organic or inorganic peroxides.

7 . Process according to any of claims 1 to 6 , characterized in that the chiral catalyst used is a chiral metal-ligand complex, where the metal is a transition metal and the ligand is a compound of the formula (III) or (IV)

where, in formula (III),

R 4 and R 5 are each independently hydrogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylphenyl, phenyl, halogen, cyano, nitro, cyano(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxycarbonyl(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl,

R 6 is (C 1 -C 6 )alkyl, halogen-, cyano-, nitro-, amino-, hydroxyl- or phenyl-substituted (C 1 -C 6 )alkyl, carboxyl, carbonyl(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxycarbonyl(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, di(C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl,

R 7 is hydrogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylphenyl, aryl, aryl(C 1 -C 6 )alkyl, preferably tert-butyl, benzyl, phenyl,

and chiral carbon atoms are designated *,

where, in formula (IV),

R 8 is hydrogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkylphenyl, phenyl, halogen, cyano, nitro, cyano(C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxycarbonyl(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl,

R 9 and R 10 are each hydrogen, (C 1 -C 6 )alkyl, phenyl, where R 9 and R 10 may form a bridge, and

chiral carbon atoms are designated *.

8 . Process according to any of claims 1 to 7 , characterized in that step (A) is followed by performing a crystallization from organic solvent or a mixture of organic solvent with water.

9 . Enantiomerically pure or enantiomerically enriched 3-triazolyl sulphoxide derivatives of the formula (I), preparable by the process according to any of claims 1 to 8 , where the enantiomer ratio is 50.5:49.5 to 99.5:0.5 (+):(−)enantiomer.