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Université de Fribourg

Photoinduced acyl transfer

Débieux, Jean-Luc ; Bochet, Christian G.

In: Journal of Physical Organic Chemistry, 2010, p. -

The acylation reaction occupies a central role in biochemistry and organic synthesis. On the one hand, it is by this very reaction that amino acids successively assemble to form peptides and proteins, and on the other hand it is a major synthetic method encompassing esterification, amidation, Friedel-Crafts reaction and many other processes routinely used both at the laboratory and the industrial...

Université de Fribourg

Preparation of photoactivable amino acid derivatives

Débieux, Jean-Luc ; Bochet, Christian G.

In: Journal of Organic Chemistry, 2009, vol. 74, no. 12, p. 4519–4524

A range of N-protected-α-amino acyl-5,7-dinitroindolines 3a−z were prepared in good yields from commercially available N-protected-α-amino acids 1a−z by a two-step sequence of acylation and intramolecular amide N-arylation. Subsequent photochemical acylation of the N-protected-α-amino acyl-5,7-dinitroindolines 3e,g,r afforded the corresponding N-protected-α-amino acid amides 22e,g,r...