Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: exploiting n-protected β-amino alcohols as alkylating agents

J Org Chem. 2015 Mar 20;80(6):3217-22. doi: 10.1021/acs.joc.5b00195. Epub 2015 Feb 26.

Abstract

The selective C3-alkylation of indoles with N-protected ethanolamines involving the "borrowing hydrogen" strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylating Agents / chemistry*
  • Amino Alcohols / chemistry*
  • Catalysis
  • Indoles / chemistry*
  • Iridium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Tryptamines / chemical synthesis*
  • Tryptamines / chemistry

Substances

  • Alkylating Agents
  • Amino Alcohols
  • Indoles
  • Organometallic Compounds
  • Tryptamines
  • tryptamine
  • Iridium