Rp. Beckett et al., APPLICATION OF THE CHIRAL AUXILIARY [(ETA(5)-C5H5)FE(CO)(PPH(3))] TO THE STEREOSELECTIVE FORMATION OF 4-SUBSTITUTED-1,4-DIHYDRONICOTINOYL COMPLEXES, Inorganica Chimica Acta, 251(1-2), 1996, pp. 265-272
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)].