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. 2010 Jan 20;132(2):460-1.
doi: 10.1021/ja909571z.

Pd(II)-catalyzed enantioselective C-H olefination of diphenylacetic acids

Bing-Feng Shi  1 , Yang-Hui Zhang, Jonathan K Lam, Dong-Hui Wang, Jin-Quan Yu
Affiliations

Pd(II)-catalyzed enantioselective C-H olefination of diphenylacetic acids

Bing-Feng Shi et al. J Am Chem Soc. .

Abstract

Pd(II)-catalyzed enantioselective C-H olefination of diphenylacetic acid substrates has been achieved through the use of monoprotected chiral amino acid ligands. The absolute configuration of the resulting olefinated products is consistent with that of a proposed C-H insertion intermediate.

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Figures

Figure 1
Figure 1
Figure 2
Figure 2
Absolute Configuration of Olefination Product 2e
Scheme 1
Scheme 1
Enantioselective C-H Activation/Olefination Using Acrylates as the Coupling Partnersa,b a The reaction conditions are identical to those described in Table 1; b The ratio of products and dr were determined by 1H NMR.
Scheme 2
Scheme 2
Derivatization of the Olefination Products
See this image and copyright information in PMC

References

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    1. Shi B-F, Maugel N, Zhang Y-H, Yu J-Q. Angew. Chem., Int. Ed. 2008;47:4761. - PubMed

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