Research Article

Trifluoromethanesulfonic Acid Catalyzed Alkylation of Arenes with Methyl (2R)-Glycidate

Pablo J. Linares-Palomino

Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA

Visiting Scientist from Dpto. Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071-Jaén, Spain.

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G. K. Surya Prakash,

G. K. Surya Prakash

Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA

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George A. Olah,

George A. Olah

Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA

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Pablo J. Linares-Palomino,

Pablo J. Linares-Palomino

Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA

Visiting Scientist from Dpto. Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071-Jaén, Spain.

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G. K. Surya Prakash,

G. K. Surya Prakash

Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA

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George A. Olah,

George A. Olah

Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA

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First published: 21 June 2005

https://doi.org/10.1002/hlca.200590102

Citations: 12

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Abstract

Methyl (R)-glycidate (=methyl (R)-oxiranecarboxylate; 2) in superacidic trifluoromethanesulfonic acid medium reacts with electron-rich arenes to give α-hydroxy-β-arylpropanoate derivatives 3a–3f with high stereospecificity. At the same time, the observed high regioselectivity has been attributed to superelectrophilic activation of the glycidate.

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Volume88, Issue6

June 2005

Pages 1221-1225

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Trifluoromethanesulfonic Acid Catalyzed Alkylation of Arenes with Methyl (2R)-Glycidate

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Trifluoromethanesulfonic Acid Catalyzed Alkylation of Arenes with Methyl (2R)-Glycidate

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