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DOI: 10.1055/s-0033-1340453
Palladium-Catalyzed Enantioselective C–H Iodination
Publication History
Publication Date:
13 December 2013 (online)
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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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