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A novel tert -butyl 2-(1-oxoisolndolin-2-yl)acetate derivative is selectively alkylated with propargyl bromide in the presence of lithium hexamethyldisilazide. After removal of the tert -butyl protecting group, the resulting N -isoindolinyl (ethynylalanine) derivative is reacted with a series of azides under 'click conditions'. The click reactions afford an array of N -isoindolinyl-1,2,3-triazolylalanine derivatives as the free carboxylic adds. Following esterification, the N -isoindolinone protecting group is then transformed into the more easily removable phthaloyl group by selective oxidation at the benzylic position.

Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues