Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines

Jordy M. Saya, Ellen D.H. van Wordragen, Romano V.A. Orru, Eelco Ruijter*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.

Original languageEnglish
Pages (from-to)5156-5160
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number31-32
Early online date3 Jan 2019
DOIs
Publication statusPublished - 1 Sep 2019

Keywords

  • Allylation
  • Boron reagents
  • Heterocycles
  • Indoles
  • Synthetic methods

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