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Issue 9, 2003
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Preparation of diamines by lithiation–substitution of imidazolidines and pyrimidines

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Abstract

The synthesis of chiral 1,2-diamines and 1,3-diamines was achieved from the unsubstituted diamines by way of N-tert-butoxycarbonyl (Boc) substituted imidazolidines (tetrahydroimidazoles) and pyrimidines (hexahydro-1,3-diazines), which were treated with sec-butyllithium to effect deprotonation α- to the N-Boc group, followed by addition of an electrophile to give substituted products that could be hydrolysed under acidic conditions to give the substituted 1,2- or 1,3-diamines. Use of the chiral ligand (−)-sparteine promoted asymmetric deprotonation of the imidazolidine substrates to give, after hydrolysis, enantiomerically enriched 1,2-diamines.

Graphical abstract: Preparation of diamines by lithiation–substitution of imidazolidines and pyrimidines

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Publication details

The article was received on 07 Feb 2003, accepted on 11 Mar 2003 and first published on 03 Apr 2003


Article type: Paper
DOI: 10.1039/B301502E
Citation: Org. Biomol. Chem., 2003,1, 1532-1544
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    Preparation of diamines by lithiation–substitution of imidazolidines and pyrimidines

    N. J. Ashweek, I. Coldham, T. F. N. Haxell and S. Howard, Org. Biomol. Chem., 2003, 1, 1532
    DOI: 10.1039/B301502E

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