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Issue 3, 2019
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Asymmetric α-alkylation of cyclic β-keto esters and β-keto amides by phase-transfer catalysis

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Abstract

Without employing any transition metal, a highly enantioselective α-alkylation of cyclic β-keto esters and β-keto amides has been realized by phase-transfer catalysis. This improved procedure is applicable to different kinds of halides with cinchona derivatives and gives the corresponding products in excellent enantiopurities (up to 98% ee) and good yields (up to 98%). Moreover, the reaction was scalable and the phase-transfer catalyst was recyclable. This provided an alternative and competitive method to the asymmetric α-alkylation of β-dicarbonyl compounds.

Graphical abstract: Asymmetric α-alkylation of cyclic β-keto esters and β-keto amides by phase-transfer catalysis

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Publication details

The article was received on 29 Oct 2018, accepted on 14 Dec 2018 and first published on 15 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02669F
Citation: Org. Biomol. Chem., 2019,17, 573-584
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    Asymmetric α-alkylation of cyclic β-keto esters and β-keto amides by phase-transfer catalysis

    Y. Wang, Y. Li, M. Lian, J. Zhang, Z. Liu, X. Tang, H. Yin and Q. Meng, Org. Biomol. Chem., 2019, 17, 573
    DOI: 10.1039/C8OB02669F

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