Issue 9, 2003
From the journal:

Organic & Biomolecular Chemistry

Preparation of diamines by lithiation–substitution of imidazolidines and pyrimidines

Neil J. Ashweek,a   Iain Coldham,*a   Thomas F. N. Haxella  and  Steven Howardb  

* Corresponding authors

a School of Chemistry, University of Exeter, Stocker Road, Exeter, UK

b GlaxoSmithKline, New Frontiers Science Park (North), Third Avenue, Harlow, Essex, UK

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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Article information

DOI
https://doi.org/10.1039/B301502E
Article type
Paper
Submitted
07 Feb 2003
Accepted
11 Mar 2003
First published
03 Apr 2003

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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