Synfacts 2009(8): 0873-0873  
DOI: 10.1055/s-0029-1217440
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Titanium-Catalyzed Asymmetric Ring Opening of meso-Aziridines

Contributor(s): Mark Lautens, Praew Thansandote
S. Peruncheralathan, H. Teller, C. Schneider*
Universität Leipzig, Germany
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Publikationsverlauf

Publikationsdatum:
23. Juli 2009 (online)

Significance

A highly enantioselective titanium-catalyzed ring opening of meso-epoxides with anilines is reported. Advantageously, the catalyst and the ligand are commercially available components that form the active catalyst in situ obviating the need for multistep catalyst or ligand preparations. The reaction is robust and facile allowing a broad scope of substrates to be transformed into 1,2-diamines in high yields and enantioselectivities. The PMP groups in the products can be selectively removed to form desirable 1,2-diamine salts.