Process for the preparation of enantiomerically enriched compounds

Process for the preparation of enantiomerically enriched compounds with formula Ar - C(R ) - C(R ) - Z wherein Ar represents an optionally substituted (hetero)aryl group, R and R , each independen tly, represent H, an alkyl, (hetero)aryl, dialkylamino, amido, thioether, alkoxy or aryloxy group with...

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Hauptverfasser: IMBOS, ROSALINDE, FERINGA, BEN, MINNAARD, ADRIAAN, JACOBUS
Format: Patent
Sprache:eng ; fre ; ger
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Zusammenfassung:Process for the preparation of enantiomerically enriched compounds with formula Ar - C(R ) - C(R ) - Z wherein Ar represents an optionally substituted (hetero)aryl group, R and R , each independen tly, represent H, an alkyl, (hetero)aryl, dialkylamino, amido, thioether, alkoxy or aryloxy group with the proviso that not both R and R represent H, or R and R 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(OR )OR or its anhydride, wherein Ar is as described above and R and R , each independently, represent H or an alkyl group, is reacted with an olefinic unsaturated compound with formula R - C = C - (R )Z, wherein R , R and Z are as described above, in the presence of a transition metal catalyst comprising a transition metal chosen from Cu and group VIII of the Periodic Table and an enantiomerically enriched ligand L, having the formula (I) where Cn together with the two O-atoms and the P-atom forms a substituted or non-substituted ring with 2-6 C-atoms, R and R each independently stand for H, an optionally substituted alkyl, aryl, alkaryl or aralkyl group, or represent the group with formula (II) wherein Cn may have the same meanings as given for Cn and B represents a bridging group, or R and R may form a heterocyclic ring together with the N-atom to which they are bound.