Synthesis 1987; 1987(12): 1110-1113
DOI: 10.1055/s-1987-28187
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

The Regiospecific Alkylation of Histidine Side Chains

J. H. Jones* , D. L. Rathbone, P. B. Wyatt
  • *The Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, UK.
Further Information

Publication History

Publication Date:
20 August 2002 (online)

Further work on the regiospecific alkylation of histidine and imidazole derivatives is reported, including convenient preparations of N(α)-benzyloxycarbonyl-N(π)-benzyl-L-histidine and N(α)-benzyloxycarbonyl-N(π)-benzyloxymethyl-L-histidine, and a sequence of reactions enabling controlled exclusive alkylation of the least hindered im-nitrogen (tritylation, phenacylation, detritylation, alkylation, and finally dephenacylation with zinc/acetic acid) in 4(5)-alkylimidazoles.