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Issue 10, 2013
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Mechanism of triflimide-catalyzed [3,3]-sigmatropic rearrangements of N-allylhydrazones—predictions and experimental validation

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Abstract

Computational analysis of the triflimide catalyzed [3,3]-sigmatropic rearrangement of N-allylhydrazones, using density functional theory calculations, is reported. Key mechanistic insight was obtained and predictions derived therefrom were confirmed experimentally through temperature dependence studies. The computational results have led to the development of electron deficient N-allylhydrazones capable of reacting under mild reaction conditions. Application of the rearrangement to form a new sp3 stereogenic center is reported for the first time.

Graphical abstract: Mechanism of triflimide-catalyzed [3,3]-sigmatropic rearrangements of N-allylhydrazones—predictions and experimental validation

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The article was received on 04 Jun 2013, accepted on 19 Jul 2013 and first published on 22 Jul 2013


Article type: Edge Article
DOI: 10.1039/C3SC51564H
Citation: Chem. Sci., 2013,4, 3997-4003
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    Mechanism of triflimide-catalyzed [3,3]-sigmatropic rearrangements of N-allylhydrazones—predictions and experimental validation

    O. Gutierrez, B. F. Strick, R. J. Thomson and D. J. Tantillo, Chem. Sci., 2013, 4, 3997
    DOI: 10.1039/C3SC51564H

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