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Issue 18, 2018
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Neighboring phenolic group-activated gem-difluoroallylboration of imines for the catalyst-free synthesis of gem-difluorohomoallylamines

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Abstract

We herein report an unprecedented addition reaction of pinacol gem-difluoroallylborates and imines enabled by a neighboring phenolic group in an N-protecting group under catalyst-free conditions, thus facilitating the construction of a wide range of racemic gem-difluorohomoallylamine derivatives. Based on the control experiments, a plausible transition state via the Zimmerman–Traxler model was proposed to elucidate the significance of the neighboring phenolic group, as well as the γ-selectivity of the boronate reagents.

Graphical abstract: Neighboring phenolic group-activated gem-difluoroallylboration of imines for the catalyst-free synthesis of gem-difluorohomoallylamines

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Publication details

The article was received on 04 Mar 2018, accepted on 11 Apr 2018 and first published on 25 Apr 2018


Article type: Communication
DOI: 10.1039/C8OB00541A
Citation: Org. Biomol. Chem., 2018,16, 3367-3371
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    Neighboring phenolic group-activated gem-difluoroallylboration of imines for the catalyst-free synthesis of gem-difluorohomoallylamines

    X. Yang, F. Zhang, Y. Zhou and Y. Huang, Org. Biomol. Chem., 2018, 16, 3367
    DOI: 10.1039/C8OB00541A

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