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

Tatsuki Takahashi, Takashi Konno, Kenichi Ogata, Shin-ichi Fukuzawa

Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

The Journal of organic chemistry 2012 Aug 3

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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.

Citation

Tatsuki Takahashi, Takashi Konno, Kenichi Ogata, Shin-ichi Fukuzawa. Stereochemistry of substitution of the α-dimethylamino group by dialkylzinc in chiral benzylferrocene. The Journal of organic chemistry. 2012 Aug 3;77(15):6638-42