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Issue 20, 2003
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Synthesis of planar chiral ferrocenyl 1,3-diamines and 1,3-amino ethers

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Abstract

The efficient syntheses of novel planar chiral 1,3-diamines and 1,3-amino ethers with an oxy or amino function directly bound to the cyclopentadienyl ring of ferrocene has been developed. The key reaction is the Cu2O promoted substitution of (pR)-N,N-diisopropyl-2-iodoferrocenecarboxamide with either phthalimide or AcOH to introduce nitrogen or oxygen functionality onto the cyclopentadienyl ring. The enantiomerically pure iodoferrocene derivative is available from the known enantioselective ortho-lithiation of N,N-diisopropylferrocenecarboxamide with n-BuLi–sparteine. In the course of these studies the synthesis of a novel C2 symmetric C-2 dimer of N,N-dimethyl-1-ferrocenylethylamine was characterised by single crystal X-ray diffraction.

Graphical abstract: Synthesis of planar chiral ferrocenyl 1,3-diamines and 1,3-amino ethers

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Publication details

The article was received on 24 Jun 2003, accepted on 15 Aug 2003 and first published on 11 Sep 2003


Article type: Paper
DOI: 10.1039/B307014J
Citation: Org. Biomol. Chem., 2003,1, 3586-3591
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    Synthesis of planar chiral ferrocenyl 1,3-diamines and 1,3-amino ethers

    J. C. Anderson, A. J. Blake and J. C. Arnall-Culliford, Org. Biomol. Chem., 2003, 1, 3586
    DOI: 10.1039/B307014J

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