Issue 10, 2013
From the journal:

Chemical Science

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

Osvaldo Gutierrez,‡b   Benjamin F. Strick,‡a   Regan J. Thomson*a  and  Dean J. Tantillo*b  

* Corresponding authors

a Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA
E-mail: r-thomson@northwestern.edu

b Department of Chemistry, University of California–Davis, 1 Shields Avenue, Davis, CA 95616, USA
E-mail: djtantillo@ucdavis.edu

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

DOI
https://doi.org/10.1039/C3SC51564H
Article type
Edge Article
Submitted
04 Jun 2013
Accepted
19 Jul 2013
First published
22 Jul 2013

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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