Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides

Akira Iwata, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Abstract Herein, we report the palladium-catalyzed cyclization reactions of indoles bearing a propargyl chloride side chain at their 3-position. In the presence of an external nucleophile, such as a sulfonamide or malonate, indoles bearing a propargyl group at their 3-position gave fused tetracyclic spiroindolines preferentially. However, in the absence of an external nucleophile, the same substrates afforded spiroindoles. Our attempts to develop a catalytic asymmetric spirocyclization onto a propargylpalladium species are also presented in this paper.

Original languageEnglish
Article number26723
Pages (from-to)6580-6585
Number of pages6
JournalTetrahedron
Volume71
Issue number37
DOIs
Publication statusPublished - 2015 Aug 7

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Bearings (structural)
Indoles
Nucleophiles
Cyclization
Palladium
Chlorides
Derivatives
Sulfonamides
Substrates

Keywords

  • Cascade cyclization
  • Catalytic asymmetric reaction
  • Palladium
  • Spiroindole

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides. / Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki.

In: Tetrahedron, Vol. 71, No. 37, 26723, 07.08.2015, p. 6580-6585.

Research output: Contribution to journalArticle

Iwata, Akira ; Inuki, Shinsuke ; Oishi, Shinya ; Fujii, Nobutaka ; Ohno, Hiroaki. / Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides. In: Tetrahedron. 2015 ; Vol. 71, No. 37. pp. 6580-6585.
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AU - Ohno, Hiroaki

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