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Synthesis 2007(1): 131-139  
DOI: 10.1055/s-2006-958927
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Cyclopropylisonitriles and their Applications in Ugi Four-Component Reactions

Anna Osipovaa, Dmitrii S. Yufitb, Armin de Meijere*a
a Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077 Göttingen, Germany
Fax: +49(551)399475; e-Mail: Armin.deMeijere@chemie.uni-goettingen.de;
b Department of Chemistry, University of Durham, South Rd., Durham, DH1 3LE, UK
e-Mail: d.s.yufit@durham.ac.uk;
Further Information

Publication History

Received 20 July 2006
Publication Date:
12 December 2006 (online)

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Abstract

Several new cyclopropylisonitriles were synthesized from the corresponding cyclopropylamines (41-69% yield) and utilized in Ugi four-component reactions to furnish 12 new dipeptides in 38-86% yield. The structures of four of these dipeptides were determined by X-ray crystallography.

Key words

ring constructions - titanium chemistry - multicomponent reactions - dipeptides - isonitriles

    References

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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited as supplementary publication no. CCDC 604790 (15b), CCDC 604791 (15d), CCDC 604792 (15h), CCDC 604703 (15i) with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.