Faculté des sciences

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... Plus

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    Summary
    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 (77−92%) under mild conditions. All these reactions occurred with complete retention of chirality as evidenced by NMR analysis. This scheme provides an attractive and alternative method to the conventional acylation of α-amino acids, especially in cases where the amide bond needs to be formed without the use of a coupling reagent.