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Synfacts 2009(4): 0424-0424  
DOI: 10.1055/s-0028-1087896
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Yttrium-Catalyzed Desymmetrization of Aziridines

Contributor(s): Mark Lautens, Jane Panteleev
B. Wu, J. C. Gallucci, J. R. Parquette*, T. V. RajanBabu*
The Ohio State University, Columbus, USA
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Publication History

Publication Date:
23 March 2009 (online)

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Significance

Asymmetric ring opening of meso-epoxides and aziridines is a valuable reaction for obtaining highly functionalized chiral building blocks. Since the early work of Nugent (J. Am. Chem. Soc. 1992, 114, 2768), Jacobsen and co-workers (J. Am. Chem. Soc. 1995, 117, 5897) and Shibasaki and co-workers (J. Am. Chem. Soc. 1997, 119, 4783), numerous reports have been published on this desymmetrization. How­ever, highly enantioselective ring opening of aziridines remains challenging. The authors report a protocol utilizing a dimeric yttrium catalyst affording enantioinduction surpassing that of previous reports.