Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes

Ming-Chang P. Yeh, Hui Fen Pai, Zao Jun Lin, Bo Ren Lee

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.

Original languageEnglish
Pages (from-to)4789-4794
Number of pages6
JournalTetrahedron
Volume65
Issue number25
DOIs
Publication statusPublished - 2009 Jun 20

Keywords

  • Cycloheptadiene
  • Cyclohexadiene
  • Gold-catalyzed
  • Hexahydroindoles
  • Hydroamination
  • Intramolecular
  • Octahydrocyclohepta[b]pyrroles
  • Sulfonamide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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