An oxidatively-activated safety catch linker for solid phase synthesis.
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.
Davies
Stephen G
SG
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. steve.davies@chem.ox.ac.uk
Mortimer
Duncan A B
DA
Mulvaney
Andrew W
AW
Russell
Angela J
AJ
Skarphedinsson
Hjalmar
H
Smith
Andrew D
AD
Vickers
Richard J
RJ
D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000737:chemistry
D010636:Phenols; D005680:gamma-Aminobutyric Acid