Patent ID: 7317126

Claim:
A method for preparing a sulphoxide compound of formula (I) either as a single enantiomer or in an enantiomerically enriched form: wherein: Y is —CN, —C(═O)X wherein X is selected from, —NR 3 R 4 , —OH, —NHNH 2 ; R 1 , R 1a , R 2 and R 2a are the same or different and are selected from H, halo, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 6 -C 10 )aryl, (C 5 -C 10 )heteroaryl, —CN, —CF 3 , —NO 2 , —OH, (C 1 -C 8 )alkoxy, —O(CH 2 ) m NR 6 R 7 , —OC(═O)R 8 , —C(═O)OR 8 , —C(═O)R 8 , —OC(═O)NR 6 R 7 , —O(CH 2 ) m OR 8 , —(CH 2 ) m OR 8 , —NR 6 R 7 , —C(═O)NR 6 R 7 ; R 3 and R 4 are the same or different and are each selected from H, (C 1 -C 6 ) alkyl, hydroxy(C 1 -C 6 )alkyl, —NHOH or —OH; R 6 and R 7 are the same or different and selected from H, (C 1 -C 6 ) alkyl, hydroxy(C 1 -C 6 )alkyl; R 8 represents H, alkyl, cycloalkyl, aralkyl, alkaryl, or aryl; n is 1, 2 or 3; and m is from 1, 2, 3, or 4; comprising the steps of: a) contacting a pro-chiral sulphide of formula (II) wherein R 1 , R 2 , R 1a , R 2a , Y and n are as defined above, with a metal chiral ligand complex, a base and an oxidizing agent in an organic solvent; and optionally b) isolating the obtained sulphoxide of formula (I); wherein said metal chiral ligand complex is selected from the group consisting of C 2 -symmetric diol titanium (IV) complexes, C 3 -symmetric trialkanolamine titanium (IV) complexes, C 3 -symmetric trialkanolamine zirconium (IV) complexes, chiral (salen) manganese (III) complexes, and chiral (salen) vanadium (IV) complexes.