Abstract
The development of a new fluorous-tagged ammonia-equivalent for the synthesis of N-alkylated amino acids is described. The required building blocks were readily accessed in high yield and purity using F-SPE purification technique. Coupling of the fluorous-tagged hydroxylamines with a selection of boronic acids and glyoxalic acid gave the desired N-alkylated amino acids. Subsequent removal of the fluorous tag via catalytic hydrogenation was investigated using a number of different catalysts and solvents. A more robust de-tagging procedure involves the transformation of the amino acid to the corresponding methyl ester followed by a Mo(CH 3CN) 3(CO) 3 mediated N–O bond cleavage.
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