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 | |
| Publication status | Published - 1997 Jan 27 |
| Externally published | Yes |
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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 journal › Article
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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 -