Preparation of diamines by lithiation–substitution of imidazolidines and pyrimidines

…, I Coldham, TFN Haxell, S Howard

Index: Ashweek, Neil J.; Coldham, Iain; Haxell, Thomas F.N.; Howard, Steven Organic and Biomolecular Chemistry, 2003 , vol. 1, # 9 p. 1532 - 1544

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Citation Number: 28

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 ...