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Synfacts 2011(7): 0745-0745
DOI: 10.1055/s-0030-1260646
DOI: 10.1055/s-0030-1260646
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Scandium-Catalyzed Asymmetric Insertion of Aryldiazomethanes
V. L. Rendina, D. C. Moebius, J. S. Kingsbury*
Boston College, Chestnut Hill, USA
Further Information
Publication History
Publication Date:
17 June 2011 (online)
![](https://www.thieme-connect.de/media/synfacts/201107/lookinside/thumbnails/10.1055-s-0030-1260646-1.jpg)
Significance
Asymmetric α-arylation of ketones can prove to be a challenge, and multistep sequences featuring asymmetric protonation are often necessary to access compounds such as 3. The authors offer an asymmetric synthesis of such α-aryl ketones through a C-C insertion of aryldiazo-methane under scandium-tris(oxazoline) ligand catalysis. The method is best suited for the synthesis of medium-sized rings, giving products in high yields and enantiomeric ratios. A model for enantioselectivity and an NMR-based proof of absolute configuration is provided.