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

Mostafa M. Amer, Ana C. Carrasco, Daniel J. Leonard, John W. Ward, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

9 Citations (Scopus)
97 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)7977-7981
Number of pages5
JournalOrganic Letters
Volume20
Issue number24
Early online date5 Dec 2018
DOIs
Publication statusPublished - 21 Dec 2018

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