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Synthesis of TFA-protected α-Amino Acid Chloride via a Vilsmeier Reagent for Friedel–Crafts Acylation
- Source :
- Letters in Organic Chemistry. 17:645-653
- Publication Year :
- 2020
- Publisher :
- Bentham Science Publishers Ltd., 2020.
-
Abstract
- α-Amino acid chlorides are reactive coupling agents in amide (peptide) formation. The Vilsmeier reagent ((chloromethylene)dimethylammonium chloride) offers a convenient way to prepare α-amino acid chlorides for peptide synthesis. Its use with N-trifluoracetyl (TFA)-protected isoleucine and allo-isoleucine is described. The 1H-NMR of the α-proton signal offers a convenient way to monitor the chirality retention in the acid chloride forming reaction and subsequent Friedel-Crafts acylation of arenes which result in α-amino acid aryl-ketone with no loss of chirality.
Details
- ISSN :
- 15701786
- Volume :
- 17
- Database :
- OpenAIRE
- Journal :
- Letters in Organic Chemistry
- Accession number :
- edsair.doi...........c3355df8d99b07ae1fff47bab2516a65