Synfacts 2007(7): 0739-0739  
DOI: 10.1055/s-2007-968612
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Cyclopropylamines

Contributor(s): Mark Lautens, Frédéric Ménard
B. Denolf, S. Mangelinckx, K. W. Törnroos, N. De Kimpe*
Ghent University, Belgium and University of Bergen, Norway
Further Information

Publication History

Publication Date:
22 June 2007 (online)

Significance

Chiral three-membered rings are important components of biologically active molecules. Although there are efficient protocols to synthesize chiral aziridines like 4, few good methods exist to prepare chiral substituted cyclopro­pylamines 3. The authors reported a simple chemodivergent procedure to access either aziridines 4 or cyclopropylamines 3 from hindered α-chloro­ketone 1. The outcome of the reaction depends solely on the basicity of the Grignard reagent used. Aryl, alkyl, and alkenyl magnesium species gave the aminocyclopropanes; only allyl magnesium bromide led to an aziridine.