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Synfacts 2010(1): 0061-0061  
DOI: 10.1055/s-0029-1218473
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Zirconium-Catalyzed Enantioselective Ring Opening of meso-Aziridines

Contributor(s): Mark Lautens, Stephen G. Newman
K. Seki, R. Yu, Y. Yamazaki, Y. Yamashita, S. Kobayashi*
The University of Tokyo, Japan
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

Optically active 1,2-diamines are commonly found in natural products, organocatalysts, ligands, resolving agents, and chiral auxiliaries. One increasingly important method for their synthesis is by ring opening of meso-aziridines. Significant progress in this transformation has been previously made by the authors utilizing ­early-transition-metal catalysis. In this report, meso-aziridines bearing an N-benzhydryl group are opened by aniline derivatives using a zirconium(IV) catalyst in the presence of a tridentate binol ligand. The protecting group can be removed by hydrogenolysis to give the monoamine-free ­diamine.