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Issue 9, 2008
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An oxidatively-activated safety catch linker for solid phase synthesis

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Abstract

A N-benzyl-4-amino-2,2-dimethylbutanoic acid-based system has been developed as a new oxidatively activated safety catch linker for reaction monitoring and optimisation on solid support. The CAN promoted oxidative debenzylation of the tertiary N-benzylamine moiety, followed by concomitant cyclisation and release of alcohols and amines has been demonstrated both in solution phase model studies and on the solid phase. The linker system has been applied to the solid phase synthesis of a collection of phenol derivatives, and to the demonstration of the attachment and release of a chiral auxiliary from a solid support.

Graphical abstract: An oxidatively-activated safety catch linker for solid phase synthesis

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Supplementary files

Article information


Submitted
07 Feb 2008
Accepted
21 Feb 2008
First published
14 Mar 2008

Org. Biomol. Chem., 2008,6, 1625-1634
Article type
Paper

An oxidatively-activated safety catch linker for solid phase synthesis

S. G. Davies, D. A. B. Mortimer, A. W. Mulvaney, A. J. Russell, H. Skarphedinsson, A. D. Smith and R. J. Vickers, Org. Biomol. Chem., 2008, 6, 1625
DOI: 10.1039/B802204F

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