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

31 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

Access to Document

10.1016/S0040-4039(96)02405-7

Cite this

@article{2c6be8a881b245a4912488d26513dabb,

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

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.",

author = "Osamu Kitagawa and Masao Fujita and Hua Li and Takeo Taguchi",

year = "1997",

month = jan,

day = "27",

doi = "10.1016/S0040-4039(96)02405-7",

language = "English",

volume = "38",

pages = "615--618",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "4",

}

TY - JOUR

T1 - Regio-controlled iodoaminocyclization reaction of an ambident nucleophile mediated by LiAl(Ot-Bu)4

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.

UR - http://www.scopus.com/inward/record.url?scp=0031013358&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0031013358&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(96)02405-7

DO - 10.1016/S0040-4039(96)02405-7

M3 - Article

AN - SCOPUS:0031013358

VL - 38

SP - 615

EP - 618

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 4

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this