Convenient synthesis of tryptophols and tryptophol homologues by hydroamination of alkynes

Vivek Khedkar, Annegret Tillack, Manfred Michalik, Matthias Beller

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70 Scopus citations

Abstract

A novel method is presented for the one-pot synthesis of substituted 3-(2-hydroxyethyl)- and 3-(3-hydroxypropyl)indoles (tryptophols and homotryptophols) from aryl hydrazines and silyl-protected ω- (hydroxyoalkyl)alkynes. Various tryptophol derivatives were prepared directly in good yield with excellent regioselectivity via a domino reaction sequence consisting of a titanium-catalyzed hydroamination of the alkyne, [3+3]-rearrangement of the resulting aryl hydrazone, and subsequent deprotection of the hydroxy group.

Original languageEnglish
Pages (from-to)7622-7631
Number of pages10
JournalTetrahedron
Volume61
Issue number32
DOIs
StatePublished - 8 Aug 2005
Externally publishedYes

Keywords

  • Amination
  • Catalysis
  • Indoles

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