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

• Published in: Journal of organic chemistry Vol. 77; no. 15; pp. 6638 - 6642
• Main Authors: Takahashi, Tatsuki, Konno, Takashi, Ogata, Kenichi, Fukuzawa, Shin-ichi
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 03.08.2012; Amer Chemical Soc
• Subjects: Acetates - chemistry; Chemistry; Chemistry, Organic; Chlorides - chemistry; Exact sciences and technology; Ferrous Compounds - chemical synthesis; Ferrous Compounds - chemistry; Metallocenes; Molecular Structure; Organic chemistry; Organometallic Compounds - chemistry; Organometalloidal and organometallic compounds; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Transition metals derivatives; Zinc - chemistry; FERROCENYL LIGANDS; Configuration inversion; Iron Organic compounds; Transition element complexes; Configuration retention; Acyl chloride; Bromine Organic compounds; Organic bromine compounds; Chiral compound; Stereochemistry; Metallocene; Chemical substitution; Ferrocene
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo3012013

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.