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Synfacts 2010(12): 1387-1387  
DOI: 10.1055/s-0030-1258893
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Arylation of N-Tosyl Ketimines

Contributor(s): Mark Lautens, Jane Panteleev
R. Shintani*, M. Takeda, T. Tsuji, T. Hayashi*
Kyoto University, Japan
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

The authors disclose an application of the rhodium diene catalyst to the addition of aryl nucleophiles to N-tosyl ketimines. These ­substrates comprise a relatively challenging class of electrophiles for asymmetric organometallic ­additions, and as a result, only a few examples of allylboronate and dialkylzinc additions are known. The resulting products are chiral amines containing a quaternary stereocenter.

Review: O. Riant, J. Hannedouche J. Org. Biomol. Chem. 2007, 5, 873-888.