Issue 38, 2005
From the journal:

Chemical Communications

Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization†

Christian V. Stevens,*a   Ellen Van Meenen,a   Yves Eeckhout,a   Bart Vanderhoydoncka  and  Wim Hooghea  

* Corresponding authors

a Research Group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, Gent, Belgium
E-mail: Chris.Stevens@Ugent.be
Fax: +32-9-264 62 43
Tel: +32-9-264 59 57

Abstract

The halogen atom transfer radical cyclization (HATRC) has been evaluated on N-(indolylmethyl)trichloroacetamides under Cu(I)Cl catalysis using nitrogen containing ligands. The ring closure leads to the formation of 3,3-spiro-3H-indoles in moderate to good yields by a 5-exo-mechanism. Derivatives with an N-electron withdrawing substituent also lead to a 5-exo-trig and not to a 6-endo-trig cyclization.

Graphical abstract: Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization

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Article information

DOI
https://doi.org/10.1039/B508424E
Article type
Communication
Submitted
16 Jun 2005
Accepted
04 Aug 2005
First published
02 Sep 2005

Chem. Commun., 2005, 4827-4829

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Synthesis of highly functionalised spiro-indoles by a halogen atom transfer radical cyclization

C. V. Stevens, E. V. Meenen, Y. Eeckhout, B. Vanderhoydonck and W. Hooghe, Chem. Commun., 2005, 4827 DOI: 10.1039/B508424E

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