Stereochemistry of Substitution of the α‑Dimethylamino Group by Dialkylzinc in Chiral Benzylferrocene

The stereochemistry of the substitution of the α-dimethylamino
group by dimethylzinc in the presence of acetyl chloride in the chiral
benzylferrocene backbone was examined. The reaction with the benzylferrocene
bearing an o-bromo substituent at both ferrocene
and the phenyl ring proceeded with inversion of configuration, while
the reaction with the benzylferrocene bearing an o-bromo substituent at either ferrocene or the phenyl ring proceeded
with retention of configuration.