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Synthesis 2009(1): 133-137  
DOI: 10.1055/s-0028-1083270
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Enantiospecific Approach to Triazolylalanine Derivatives

Clare E. Jamookeeaha, Christopher D. Beadleb, Joseph P. A. Harrity*a
a Department of Chemistry, University of Sheffield, Sheffield, S3 7HF, UK
Fax: +44(114)2229346; e-Mail: j.harrity@sheffield.ac.uk;
b Eli Lilly and Company Ltd, Lilly Research Centre, Erl Wood Manor, Windlesham, Surrey, GU20 6PH, UK
Further Information

Publication History

Received 8 October 2008
Publication Date:
12 December 2008 (online)

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Abstract

An efficient and practical route to an enantiomerically pure aziridinylmethyl azide is described that can be transformed to the corresponding triazole by a copper-catalysed [3+2] alkyne cycloaddition reaction. The transformation of these intermediates into triazolylalanine-type derivatives by aziridine ring-opening reactions is also described.

Key words

copper catalyst - 1,2,3-triazole - aziridine - cycloaddition - ring-opening reaction - alanine

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10

Whilst the product ee values were not determined, we have previously shown that nucleophilic additions to 3 and subsequent manipulations preserve stereochemical integrity and hence assume that these processes are enantiospecific.