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Synfacts 2014; 10(1): 0046
DOI: 10.1055/s-0033-1340453
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Enantioselective C–H Iodination

Contributor(s):
Mark Lautens
,
Christine M. Le
Chu L, Wang X.-C, Moore CE, Rheingold AL, Yu J.-Q * The Scripps Research Institute, La Jolla and The University of California, San Diego, La Jolla, USA
Pd-Catalyzed Enantioselective C–H Iodination: Asymmetric Synthesis of Chiral Diarylmethylamines.

J. Am. Chem. Soc. 2013;
135: 16344-16347
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

palladium - C–H iodination - desymmetrization - diarylmethylamines

Significance

The diarylmethylamine motif is present in a range of biologically active compounds. Methods aimed at the enantioselective synthesis of diarylmethylamines include 1,2-addition of organometallic species to aldimines (see Review) and asymmetric hydrogenation of the corresponding imines (J. Am. Chem. Soc. 2010, 132, 2124). Here, the authors report the asymmetric synthesis of diarylmethylamines via palladium-­catalyzed desymmetrizing C–H iodination. This ­report is the first example of an asymmetric C–H iodination in the absence of a chiral auxiliary.


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Comment

The iodination of ortho-substituted substrates proceeds with good yields and excellent enantioselectivities. However, in the absence of ortho substituents, a significant amount of the diiodinated product is obtained. Interestingly, the enantioselectivity of the di-iodinated product remains consistently higher than that of the mono-iodinated product.


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Review

M. T. Robak, M. A. Herbage, J. A. Ellman Chem. Rev. 2010, 110, 3600–3740.


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