Issue 70, 2012
From the journal:

Chemical Communications

Cu(i)-catalyzed atom transfer radical cyclization of trichloroacetamides tethered to electron-deficient, -neutral, and -rich alkenes: synthesis of polyfunctionalized 2-azabicyclo[3.3.1]nonanes†

Faïza Diaba,a   Agustín Martínez-Laporta,a   Josep Bonjoch,*a   Ana Pereira,b   José María Muñoz-Molina,b   Pedro J. Pérezb  and  Tomás R. Belderrain*b  

* Corresponding authors

a Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain
E-mail: josep.bonjoch@ub.edu
Tel: +34 934024540

b Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al CSIC, CIQSO, Universidad de Huelva, Campus de El Carmen, 21007 Huelva, Spain
E-mail: trodri@uhu.es
Tel: +34 959219955

Abstract

A novel synthetic entry to 2-azabicyclo[3.3.1]nonanes based on a copper(I)-catalyzed intramolecular coupling of amino-tethered trichloroacetamides and unsaturated nitriles, esters and alkenes, as well as enol acetates, is described. A study of the reaction conditions and the scope of the process is reported.

Graphical abstract: Cu(i)-catalyzed atom transfer radical cyclization of trichloroacetamides tethered to electron-deficient, -neutral, and -rich alkenes: synthesis of polyfunctionalized 2-azabicyclo[3.3.1]nonanes

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Article information

DOI
https://doi.org/10.1039/C2CC34133F
Article type
Communication
Submitted
07 May 2012
Accepted
13 Jul 2012
First published
13 Jul 2012

Chem. Commun., 2012,48, 8799-8801

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Cu(I)-catalyzed atom transfer radical cyclization of trichloroacetamides tethered to electron-deficient, -neutral, and -rich alkenes: synthesis of polyfunctionalized 2-azabicyclo[3.3.1]nonanes

F. Diaba, A. Martínez-Laporta, J. Bonjoch, A. Pereira, J. M. Muñoz-Molina, P. J. Pérez and T. R. Belderrain, Chem. Commun., 2012, 48, 8799 DOI: 10.1039/C2CC34133F

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