| Item type |
学術雑誌論文 / Journal Article(1) |
| 公開日 |
2007-05-11 |
| タイトル |
|
|
タイトル |
Construction of Terminal Conjugated Enynes: Cu-Mediated Cross-Coupling Reaction of Alkenyldialkylborane with (Trimethylsilyl)ethynyl Bromide |
|
言語 |
en |
| 言語 |
|
|
言語 |
eng |
| 資源タイプ |
|
|
資源 |
http://purl.org/coar/resource_type/c_6501 |
|
タイプ |
journal article |
| アクセス権 |
|
|
アクセス権 |
open access |
|
アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 著者 |
Hoshi, Masayuki
Kawamura, Noritsugu
Shirakawa, Kazuya
|
| 著者別名 |
|
|
|
識別子Scheme |
WEKO |
|
|
識別子 |
44871 |
|
|
識別子Scheme |
KAKEN |
|
|
識別子URI |
https://nrid.nii.ac.jp/ja/nrid/1000000113712 |
|
|
識別子 |
113712 |
|
|
姓名 |
星, 雅之 |
|
|
言語 |
ja |
| 抄録 |
|
|
内容記述タイプ |
Abstract |
|
内容記述 |
The cross-coupling reaction of (E)- and (Z)-alk-1-enyldialkylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a catalytic amount of Cu(acac)_2 and a base under extremely mild conditions to provide conjugated enynes whose carbon-carbon triple bond is distal position. The use of 1M NaOMe as the base results in not only cross-coupling but also desilylation affording both (E)- and (Z)-alk-3-en-1-ynes exclusively, while the use of LiOH･H_2O instead of 1M NaOMe preferentially gives both (E)- and (Z)-1-(trimethylsilyl)alk-3-en-1-ynes with high regio- and stereoselectivity. On the other hand, the cross-coupling reaction of (Z)-1-(trimethylsilyl)alk-1-enyldicyclohexylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a small amount of CuI and aqueous NaOH under extremely mild conditions to afford (Z)-1,3-bis(trimethylsilyl)alk-3-en-1-yne with high regio- and stereoselectivity. In addition, treatment of the resultant product with 1M NaOMe leads to the stereoselective formation of (Z)-3-(trimethylsilyl)alk-3-en-1-yne in a one-pot manner. |
| 書誌情報 |
Synlett
巻 2006,
号 12,
p. 1961-1970,
発行日 2006-06
|
| DOI |
|
|
|
識別子タイプ |
DOI |
|
|
関連識別子 |
http://doi.org/10.1055/s-2006-942373 |
| 権利 |
|
|
権利情報 |
http://www.thieme-connect.de/ejournals/abstract/synthesis/doi/10.1055/s-2006-942373 |
| 権利 |
|
|
権利情報 |
Georg Thieme Verlag, M.Hoshi, K.Shirakawa, Synlett, 2006(12), 2006, 1961-1970. c 2006 Georg Thieme Verlag KG. |
| フォーマット |
|
|
内容記述タイプ |
Other |
|
内容記述 |
application/pdf |
| 出版者 |
|
|
出版者 |
Georg Thieme Verlag |
|
言語 |
en |
| 著者版フラグ |
|
|
言語 |
en |
|
値 |
author |
| 出版タイプ |
|
|
出版タイプ |
AM |
|
出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
5113.pdf (348.1 kB)
