Iodocarbocyclization and iodoaminocyclization reactions mediated by a metallic reagent

Osamu Kitagawa, Takeo Taguchi

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

We have developed new iodine-mediated carbocyclization and aminocyclization reactions through activation of intramolecular carbon or amide nucleophiles by metallic reagents. In the presence of 12 and Ti(OR)4 or TiCl4-Et3N, iodocarbocyclization of various active methine compounds having alkenyl or alkynyl groups proceeded in a highly stereospecific manner to give iodocyclo-alkanes or -alkenes in good yields. The present reaction can be also applied to asymmetric catalytic reaction; that is, the reaction of 4-alkenylmalonate derivatives with Ti(TADDOLate)2 catalyst gave iodoalkylcyclopentanes with excellent enantioselectivity (> 95%ee). Furthermore, iodoaminocyclization of unsaturated amide derivatives with an ambident nucleophilic center and iodoaziridination of N-allylic tosylamides, featuring regiocontrol and an activation of an amide nucleophile by a basic metallic reagent, were also established.

Original languageEnglish
Pages (from-to)1191-1199
Number of pages9
JournalSynlett
Issue number8
Publication statusPublished - 1999
Externally publishedYes

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Amides
Nucleophiles
Chemical activation
Derivatives
Alkanes
Enantioselectivity
Alkenes
Iodine
Carbon
Catalysts
titanium tetrachloride

Keywords

  • Catalytic asymmetric reaction
  • Iodine
  • Iodoaminocyclization
  • Iodocarbocyclization
  • Metallic reagent

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Iodocarbocyclization and iodoaminocyclization reactions mediated by a metallic reagent. / Kitagawa, Osamu; Taguchi, Takeo.

In: Synlett, No. 8, 1999, p. 1191-1199.

Research output: Contribution to journalArticle

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