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.
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
Tatsuki
T
Takahashi
Takashi
T
Konno
Kenichi
K
Ogata
Shin-ichi
S
Fukuzawa
D000085:Acetates / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D000075163:Metallocenes; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000085:Acetates; D002712:Chlorides; D005296:Ferrous Compounds; D000075163:Metallocenes; D009942:Organometallic Compounds; D015032:Zinc; C081124:acetyl chloride; C004998:ferrocene