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Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)7977-7981
Number of pages5
JournalOrganic Letters
Issue number24
Early online date5 Dec 2018
DateAccepted/In press - 5 Dec 2018
DateE-pub ahead of print - 5 Dec 2018
DatePublished (current) - 21 Dec 2018


Imidazolidinone derivatives of a range of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler-Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C=O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones and their congeners in enantioenriched form.



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