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The Journal of organic chemistry

Stereochemistry of substitution of the α-dimethylamino group by dialkylzinc in chiral benzylferrocene.


PMID 22799888

Abstract

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.