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Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)5770-5773
Number of pages4
JournalOrganic Letters
Issue number18
Early online date11 Sep 2018
DateAccepted/In press - 11 Sep 2018
DateE-pub ahead of print - 11 Sep 2018
DatePublished (current) - 21 Sep 2018


The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.

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