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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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Article information


Submitted
04 Jun 2013
Accepted
19 Jul 2013
First published
22 Jul 2013

Chem. Sci., 2013,4, 3997-4003
Article type
Edge Article

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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