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

Osamu Kitagawa; Masao Fujita; Hua Li; Takeo Taguchi

doi:10.1016/S0040-4039(96)02405-7

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 journal › Article › peer-review

32 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 language	English
Pages (from-to)	615-618
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4039(96)02405-7
Publication status	Published - 1997 Jan 27
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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AU - Kitagawa, Osamu

AU - Fujita, Masao

AU - Li, Hua

AU - Taguchi, Takeo

PY - 1997/1/27

Y1 - 1997/1/27

N2 - 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.

AB - 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.

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

Abstract

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