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Issue 25, 2013
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Aniline mediated oxidative C–C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(D)-amino acid derivatives

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Abstract

A metal-free and 4-methyl aniline mediated method for the oxidative C–C bond cleavage has been developed. The reaction proceeds in air using molecular oxygen as the oxidant, affording one-carbon shortened esters in moderate to good yields within a short time. Moreover, it provides a model reaction for the highly enantioselective synthesis of (D)-serine esters by combining with a L-proline catalyzed Mannich reaction.

Graphical abstract: Aniline mediated oxidative C–C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(d)-amino acid derivatives

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Publication details

The article was received on 05 Apr 2013, accepted on 13 May 2013 and first published on 14 May 2013


Article type: Communication
DOI: 10.1039/C3OB40685G
Citation: Org. Biomol. Chem., 2013,11, 4138-4141
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    Aniline mediated oxidative C–C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(D)-amino acid derivatives

    B. Hu, Y. Li, Z. Li and X. Meng, Org. Biomol. Chem., 2013, 11, 4138
    DOI: 10.1039/C3OB40685G

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