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Synthesis and Structure of an Enantiomerically Pure C 2 Symmetric Ferrocenyl Carbene
Author(s) -
Broggini Diego,
Togni Antonio
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200208)85:8<2518::aid-hlca2518>3.0.co;2-n
Subject(s) - chemistry , carbene , deprotonation , ferrocene , silylation , imidazole , amine gas treating , yield (engineering) , trimethylsilyl , nucleophile , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ion , materials science , electrode , metallurgy , electrochemistry
The straightforward, high‐yield synthesis and X‐ray structural analysis of the air‐stable planar‐chiral bis(ferrocenyl)carbene 1,3‐bis‐{(1 R )‐1‐[(1 R )‐1‐(trimethylsilyl)ferrocen‐2‐yl]ethyl}imidazol‐2‐ylidene ( 5 ) is reported. Compound 5 is obtained in four steps from the amine [(1 R )‐1‐(dimethylamino)ethyl]ferrocene ( 1 ) upon diastereoselective silylation, methylation, nucleophilic substitution by imidazole, and deprotonation. The X‐ray crystal structure of the free carbene shows the typical conformational features of the 1,2‐disubstituted ferrocenyl units, as found in other ferrocenyl ligands derived from 1 .