Regiocontrolled Iodoaminocyclization Reaction of an Ambident Nucleophile Mediated by Basic Metallic Reagent

Masao Fujita, Osamu Kitagawa, Takashi Suzuki, Takeo Taguchi

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

A new and general method of iodine-mediated cyclization reactions of allyl or homoallyl carbamates, ureas, and amides was found to give N-cyclized products as single regioisomers. The present reaction proceeded in good yield through regiocontrol (N-cyclization > O-cyclization) and the increase in the reactivity of an ambident nucleophile by a basic metallic reagent. The N-cyclization selectivity was remarkably affected by the additive employed. The iodoaminocyclization reaction of the homoallyl carbamates and ureas with a chiral center at the homoallylic position was found to proceed with high 1,3-cis- and 1,3-trans-selectivity, respectively.

Original languageEnglish
Pages (from-to)7330-7335
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number21
Publication statusPublished - 1997
Externally publishedYes

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Nucleophiles
Cyclization
Carbamates
Urea
Amides
Iodine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Regiocontrolled Iodoaminocyclization Reaction of an Ambident Nucleophile Mediated by Basic Metallic Reagent. / Fujita, Masao; Kitagawa, Osamu; Suzuki, Takashi; Taguchi, Takeo.

In: Journal of Organic Chemistry, Vol. 62, No. 21, 1997, p. 7330-7335.

Research output: Contribution to journalArticle

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