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Synthesis 2009(18): 3120-3126  
DOI: 10.1055/s-0029-1219617
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

On the Synthesis of Asymmetric and Dissymmetric Amino Analogues of ­Tröger’s Base

Josep Artacho, Kenneth Wärnmark*
Organic Chemistry, Department of Chemistry, Lund University, P. O. Box 124, 221 00 Lund, Sweden
Fax: +46(46)2228209; e-Mail: Kenneth.Warnmark@organic.lu.se;
Further Information

Publication History

Received 19 March 2009
Publication Date:
23 July 2009 (online)

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Abstract

Monoamino and diamino analogues of Tröger’s base have been synthesized by palladium-catalyzed aminations of the corresponding dihalo analogues using low catalyst loadings. Depending on the nature of the dihalo analogue (Br or I), catalyst loading and the scale of the reaction, monoamino-monohalo and/or diamino analogues of Tröger’s base were obtained.

Key words

aminations - catalysis - palladium - Tröger’s base - halogen-lithium exchange

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