Regio-controlled iodoaminocyclization reaction of an ambident nucleophile mediated by LiAl(Ot-Bu)4

Osamu Kitagawa, Masao Fujita, Hua Li, Takeo Taguchi

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

A new and general method of iodine-mediated cyclization reactions of unsaturated carbamates, ureas and amides which gives N-cyclized products as a single regio-isomer was achieved. The present reaction proceeds in good yield through regio-control of an ambident nucleophile by LiAl(Ot-Bu)4, and the regio-control (N-attack vs O-attack) was also found to be remarkably affected by the additive employed.

Original languageEnglish
Pages (from-to)615-618
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number4
DOIs
Publication statusPublished - 1997 Jan 27
Externally publishedYes

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Nucleophiles
Carbamates
Cyclization
Amides
Iodine
Isomers
Urea

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Regio-controlled iodoaminocyclization reaction of an ambident nucleophile mediated by LiAl(Ot-Bu)4. / Kitagawa, Osamu; Fujita, Masao; Li, Hua; Taguchi, Takeo.

In: Tetrahedron Letters, Vol. 38, No. 4, 27.01.1997, p. 615-618.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Fujita, Masao ; Li, Hua ; Taguchi, Takeo. / Regio-controlled iodoaminocyclization reaction of an ambident nucleophile mediated by LiAl(Ot-Bu)4. In: Tetrahedron Letters. 1997 ; Vol. 38, No. 4. pp. 615-618.
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