PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS

摘要

Process for the preparation of enantiomerically enriched compounds of formula Ar-C(R¹)-C(R²)-Z wherein Ar represents an optionally substituted (hetero)aryl group R¹ and R², each independently, represent H, an alkyl, (hetero)aryl, dialkylamino, amido, thioether, alkoxy or aryloxy group with the proviso that not both R¹ and R² represent H, or R¹ and R² form together with the C-atoms to which they are bound a (hetero)alkyl or (hetero)alkenyl ring and Z represents an electron withdrawing group, in which process a boronic acid derivate of formula Ar-B(OR³)OR⁴ or its anhydride, wherein R³ and R⁴, each independently, represent H or an alkyl group, is reacted with an olefinic unsaturated compound of formula R²-C-C-(R¹)Z in the presence of a transition metal catalyst comprising a transition metal chosen from Cu and group VIII and an enantiomerically enriched ligand L, having formula (I) where C_n together with the two O-atoms and the P-atom forms a substituted or nonsubstituted ring with 2-6 C-atoms, R⁵ and R⁶ each independently represent H, an optionally substituted alkyl, aryl, alkaryl, or aralkyl group, or the group of formula (II) wherein C_n¹ may have the same meanings as given for C_n and B represents a bridging group, or R⁵ and R⁶ may form a heterocyclic ring together with the N-atom to which they are bound.