Enantioselective C2-Alkylation of Indoles through a Redox-Relay Heck Reaction of 2-Indole Triflates

Nicholas J. Race, Qianjia Yuan, Matthew S. Sigman

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A palladium-catalyzed enantioselective redox-relay Heck reaction of 2-indole triflates and disubstituted alkenes is reported. This process combines readily available indole triflates with a variety of alkenes to afford a range of indole derivatives bearing a stereocenter adjacent to C2. Enantioselectivity is achieved through use of a simple pyridine-oxazoline ligand. Tuning the electronics of the indole, through judicious choice of N-protecting group, is required to ensure selective β-hydride elimination away from the indole core. Utility of this method is highlighted in a modular formal synthesis of an S1P1 agonist precursor developed by Merck.

Original languageEnglish (US)
Pages (from-to)512-515
Number of pages4
JournalChemistry - A European Journal
Volume25
Issue number2
DOIs
StatePublished - Jan 7 2019
Externally publishedYes

Bibliographical note

Funding Information:
The work was supported by National Institute of Health (NIGMS R01GM063540). Q.Y. acknowledges Shanghai Jiao Tong University for a postdoctoral fellowship.

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Heck reaction
  • asymmetric catalysis
  • enantioselective catalysis
  • indole
  • palladium

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