A visible light-mediated, decarboxylative, desulfonylative Smiles rearrangement for general arylethylamine syntheses.
Chem Commun (Camb)
; 56(77): 11493-11496, 2020 Sep 29.
Article
em En
| MEDLINE
| ID: mdl-32857086
ABSTRACT
A decarboxylative, desulfonylative Smiles rearrangement is presented that employs activated-ester/energy transfer catalysis to decarboxylate ß-amino acid derived starting materials at room-temperature under visible light irradiation. The radical Smiles rearrangement gives a range of biologically active arylethylamine products highly relevant to the pharmaceutical industry, chemical biology and materials science. The reaction is then applied to the synthesis of a chiral unnatural amino acid, 2-thienylalanine, used in the treatment of phenylketonuria. We also show how the reaction can proceed under metal-free and catalyst-free conditions.
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MEDLINE
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En
Ano de publicação:
2020
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Article