| Item type |
学術雑誌論文 / Journal Article(1) |
| 公開日 |
2017-10-04 |
| タイトル |
|
|
タイトル |
Synthesis of nitrogen-containing heterocycles using exo- and endo-selective radical cyclizations onto enamides |
| 言語 |
|
|
言語 |
eng |
| 資源タイプ |
|
|
資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
|
資源タイプ |
journal article |
| ID登録 |
|
|
ID登録 |
10.24517/00014965 |
|
ID登録タイプ |
JaLC |
| 著者 |
Taniguchi, Tsuyoshi
Yonei, Daigo
Sasaki, Masamichi
Tamura, Osamu
Ishibashi, Hiroyuki
|
| 著者別表示 |
谷口, 剛史
田村, 修
石橋, 弘行
|
| 提供者所属 |
|
|
内容記述タイプ |
Other |
|
内容記述 |
金沢大学ナノ生命科学研究所 / 金沢大学大学院自然科学研究科生理活性物質科学 |
| 書誌情報 |
Tetrahedron
巻 64,
号 11,
p. 2634-2641,
発行日 2008-03-10
|
| ISSN |
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収録物識別子タイプ |
ISSN |
|
収録物識別子 |
0040-4020 |
| NCID |
|
|
収録物識別子タイプ |
NCID |
|
収録物識別子 |
AA00861787 |
| DOI |
|
|
関連タイプ |
isVersionOf |
|
|
識別子タイプ |
DOI |
|
|
関連識別子 |
10.1016/j.tet.2008.01.016 |
| 出版者 |
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出版者 |
Elsevier |
| 抄録 |
|
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内容記述タイプ |
Abstract |
|
内容記述 |
The effect of positional change of the carbonyl group of enamides on Bu3SnH-mediated alkyl radical cyclization leading to five-, six-, seven-, and eight-membered nitrogen-containing heterocycles was examined. A 5-exo cyclization is generally preferred over a 6-endo ring closure in systems having an alkyl radical center on the enamide-acyl side chain, whereas enamides having an alkyl radical center opposite to the acyl side chain predominantly gave 6-endo cyclization products. These results suggest that the exo or endo selectivity of radical cyclization onto the alkenic bond of enamides can be controlled by positional change of the carbonyl group. For an understanding of these selectivities, heat of formation for each transition state was calculated. 6-endo-Selective radical cyclization was applied to the radical cascade, enabling a concise synthesis of a cylindricine skeleton. A 7- or 8-endo alkyl radical cyclization, however, predominated over a corresponding 6- or 7-exo ring closure regardless of the positional change of the carbonyl group of enamides. © 2008 Elsevier Ltd. All rights reserved. |
| 著者版フラグ |
|
|
出版タイプ |
AM |
|
出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
PH-PR-ISHIBASHI-H-2634.pdf (223.9 kB)
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