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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.

Original publication

DOI

10.1039/b802204f

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/05/2008

Volume

6

Pages

1625 - 1634

Keywords

Combinatorial Chemistry Techniques, Cyclization, Molecular Structure, Oxidation-Reduction, Phenols, Stereoisomerism, gamma-Aminobutyric Acid