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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
Volume20
Issue number24
Early online date5 Dec 2018
DOIs
DateAccepted/In press - 5 Dec 2018
DateE-pub ahead of print - 5 Dec 2018
DatePublished (current) - 21 Dec 2018

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.

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    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/acs.orglett.8b03551 . Please refer to any applicable terms of use of the publisher.

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