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

Jessica E. Hill, Quentin Lefebvre, Laura A. Fraser, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

4 Citations (Scopus)
208 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)5770-5773
Number of pages4
JournalOrganic Letters
Volume20
Issue number18
Early online date11 Sep 2018
DOIs
Publication statusPublished - 21 Sep 2018

Structured keywords

  • BCS and TECS CDTs

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