engleski

Photodecarboxylation of amino acids activated by phthalimide

Azomethine ylides are 1, 3-dipoles which can be generated from many sources, including aziridines, imines, and iminiums.1 Another way of azomethine ylide generation, which attracted our attention, is photochemical decarboxylation reaction of N-phthaloyl α-amino acids.2 For example, irradiation of N-phthaloylglycine (1) in acetonitrile generates azomethine ylide 1-AY, which subsequently undergo [3+2] reaction with acrylonitrile to form cycloadducts 2, along with formation of N-methylphthalimide (3). Within the scope of our investigation on photodecarboxylation of amino acids derived from different cage molecules and activated with phthalimide chromophore, 3 we turned our attention to potential [3+2] cycloaddition with phthalimide derivatives 4 and 5. However, preliminary photochemical reactions of 4 and 5 in solution in the presence of acrylonitrile gave only simple decarboxylation products. To circumvent this problem, it is planned to use supramolecular control of the photochemical reaction. Complexation of 1, 4 and 5 with various macrocyclic hosts, such as cyclodextrins and cucurbit[n]urils, is anticipated to enable [3+2] cycloadditions with photochemically generated azomethine ylides.

photochemistry; supramolecular chemistry; azomethine ylides

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