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. 2012 Feb 17;17(2):1992-9.
doi: 10.3390/molecules17021992.

Allylic alkylations catalyzed by palladium-bis(oxazoline) complexes derived from heteroarylidene malonate derivatives

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Allylic alkylations catalyzed by palladium-bis(oxazoline) complexes derived from heteroarylidene malonate derivatives

Lei Liu et al. Molecules. .

Abstract

A series of simple heteroarylidene malonate-type bis(oxazoline) ligands 4 and 5 were applied to the palladium-catalyzed allylic alkylation reaction, and the ligand 4a bearing a phenyl group afforded excellent enantioselectivity (up to 96% ee) for the allylic alkylation product. Other substrates were also examined, giving the allylic alkylated products in high yield but with poor ee values.

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Figures

Figure 1
Figure 1
The alkylidene and arylidene malonate-type bis(oxazoline) ligands.
Scheme 1
Scheme 1
The model reaction of palladium-catalyzed asymmetric allylic alkylation.

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References

    1. Trost B.M., van Vranken D.L. Asymmetric transition metal-catalyzed allylic alkylations. Chem. Rev. 1996;96:395–422. - PubMed
    1. Johannsen M., Jørgensen K.A. Allylic amination. Chem. Rev. 1998;98:1689–1708. doi: 10.1021/cr970343o. - DOI - PubMed
    1. Helmchen G., Pfaltz A. Phosphinooxazolines—A new class of versatile, modular P,N-ligands for asymmetric catalysis. Accounts Chem. Res. 2000;33:336–345. - PubMed
    1. Trost B.M., Crawley M.L. Asymmetric transition-metal-catalyzed allylic alkylations: Applicationsin total synthesis. Chem. Rev. 2003;103:2921–2944. doi: 10.1021/cr020027w. - DOI - PubMed
    1. Lu Z., Ma S. Metal-catalyzed enantioselective allylation in asymmetric synthesis. Angew.Chem. Int. Ed. 2008;47:258–297. doi: 10.1002/anie.200605113. - DOI - PubMed

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