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Issue 6, 2017
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Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid

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Abstract

By utilizing the recently developed EATA (enantioselective allenylation of terminal alkynes) reaction and the aerobic oxidation of alcohols, lamenallenic acid, a naturally occurring axially chiral allene, has been synthesized with a high ee value and E/Z selectivity from methyl 5-hexynoate and (E)-10-dodecenal, which could be prepared easily from 1-decyne and 1-pentyne, respectively, with (S)-α,α-dimethylprolinol as the chiral source.

Graphical abstract: Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid

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Publication details

The article was received on 07 Dec 2016, accepted on 06 Feb 2017 and first published on 08 Feb 2017


Article type: Research Article
DOI: 10.1039/C6QO00785F
Citation: Org. Chem. Front., 2017,4, 951-957
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    Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid

    X. Jiang, Y. Xue and S. Ma, Org. Chem. Front., 2017, 4, 951
    DOI: 10.1039/C6QO00785F

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