Issue 20, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-aminoalkyl radicals†

Mark E. Wood,*a   Sabine Bissiriou,a   Christopher Lowe,b   Andrew M. Norrish,a   Katell Sénéchal,a   Kim M. Windeatt,a   Simon J. Colesc  and  Michael B. Hursthousec  

* Corresponding authors

a School of Biosciences, University of Exeter, Geoffrey Pope Building, Stocker Road, Exeter, UK
E-mail: m.e.wood@exeter.ac.uk
Tel: +44 1392 263450

b UCB Celltech, 208 Bath Road, Berkshire, Slough, UK

c EPSRC X-ray Crystallography Service, Department of Chemistry, University of Southampton, Southampton, Highfield, UK

Abstract

The extent to which deuterium can act as a protecting group to prevent unwanted 1,5-hydrogen atom transfer to aryl and vinyl radical intermediates was examined in the context of the generation of α-aminoalkyl radicals in a pyrrolidine ring. Intra- and intermolecular radical trapping following hydrogen atom transfer provides an illustration of the use of the primary kinetic isotope effect in directing the outcome of synthetic C–C bond-forming processes.

Graphical abstract: Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-aminoalkyl radicals

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Article information

DOI
https://doi.org/10.1039/C0OB00205D
Article type
Paper
Submitted
04 Jun 2010
Accepted
05 Jul 2010
First published
17 Aug 2010

Org. Biomol. Chem., 2010,8, 4653-4665

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Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-aminoalkyl radicals

M. E. Wood, S. Bissiriou, C. Lowe, A. M. Norrish, K. Sénéchal, K. M. Windeatt, S. J. Coles and M. B. Hursthouse, Org. Biomol. Chem., 2010, 8, 4653 DOI: 10.1039/C0OB00205D

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