Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 20, 2003
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

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
  •   Request permissions

    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

Search articles by author