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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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Publication details

The article was received on 07 Feb 2008, accepted on 21 Feb 2008 and first published on 14 Mar 2008


Article type: Paper
DOI: 10.1039/B802204F
Citation: Org. Biomol. Chem., 2008,6, 1625-1634
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    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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