Preparation of photoactivable amino acid derivatives
- Débieux, Jean-Luc Department of Chemistry, University of Fribourg, Switzerland
- Bochet, Christian G. Department of Chemistry, University of Fribourg, Switzerland
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28.05.2009
Published in:
- Journal of Organic Chemistry. - 2009, vol. 74, no. 12, p. 4519–4524
English
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.
- Faculty
- Faculté des sciences et de médecine
- Department
- Département de Chimie
- Language
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 13143
- DOI 10.1021/jo900442p
- Persistent URL
- https://folia.unifr.ch/unifr/documents/301208
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