Synthesis 2009(1): 97-104  
DOI: 10.1055/s-0028-1083279
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The Direct Synthesis of Unsymmetrical Vicinal Diamines from Terminal Alkynes: A Tandem Sequential Approach for the Synthesis of Imidazolidinones

Alison V. Leea, Melanie Sajitzb, Laurel L. Schafer*a
a Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada
e-Mail: Schafer@chem.ubc.ca;
b Organisch-Chemisches Institut, Wesfälische Wilhelms-Universität, Corrensstr. 40, 48149 Münster, Germany
Further Information

Publication History

Received 23 October 2008
Publication Date:
12 December 2008 (online)

Abstract

The combination of titanium-catalyzed anti-Markovni­kov hydroamination of terminal alkynes with the Strecker reaction is used in the synthesis of unsymmetrical vicinal diamines via the one-pot synthesis of α-cyanoamines. This methodology is further applied to the efficient synthesis of imidazolidinones. An easy-to-use bis(amidate)titanium precatalyst permits efficient approaches to heterocyclic chemistry from terminal alkynes.