Article ID Journal Published Year Pages File Type
5220996 Tetrahedron 2011 7 Pages PDF
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(CH3CN)3(CO)3 mediated N-O bond cleavage.

Graphical abstractDownload full-size image

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
Authors
, , , ,