APPLICATION OF THE CHIRAL AUXILIARY [(ETA(5)-C5H5)FE(CO)(PPH(3))] TO THE STEREOSELECTIVE FORMATION OF 4-SUBSTITUTED-1,4-DIHYDRONICOTINOYL COMPLEXES

In solution regio- and stereoselective additions of nucleophiles to (R S)-[(eta(5)-C5H5)Fe(CO)(PPh(3))CO-3-pyridyl] (1) occur at C-4 to give the corresponding nitrogen-stabilised anions. Subsequent quenching of these anions by a proton, a chloroformate or dimethyl sulfate gives th e corresponding 1,4-dihydropyridine complexes as single diastereoisome rs. The predicted stereochemical course of the nucleophilic additions is confirmed by a single crystal X-ray structure determination of -(N- methoxycarbonyl-4-methyl-1,4-dihydropyridyl)].