Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates

Santanu Panda, Joseph M. Ready

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)6038-6041
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number17
DOIs
StatePublished - May 3 2017

Fingerprint

Indoles
Regioselectivity
Palladium
Esters
Acetates
Catalysts
indole
indoline
2-naphthol BINAP

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates. / Panda, Santanu; Ready, Joseph M.

In: Journal of the American Chemical Society, Vol. 139, No. 17, 03.05.2017, p. 6038-6041.

Research output: Contribution to journalArticle

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