WEKO3
-
RootNode
アイテム
Palladium-Catalyzed Sequential Twofold Nucleophilic Substitution on 3-Bromopenta-2,4-dienyl Phosphate : Preparation of C1- and C2-Symmetric Doubly Functionalized Allenes
https://tokushima-u.repo.nii.ac.jp/records/2007013
https://tokushima-u.repo.nii.ac.jp/records/2007013e78ba3bb-0117-4ce7-880f-05d2f87629a3
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
joc_84_19_12463.pdf (1.07 MB)
|
|
| Item type | 文献 / Documents(1) | |||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 公開日 | 2019-12-19 | |||||||||||||
| アクセス権 | ||||||||||||||
| アクセス権 | open access | |||||||||||||
| 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 | |||||||||||||
| 出版社版DOI | ||||||||||||||
| 関連識別子 | https://doi.org/10.1021/acs.joc.9b01933 | |||||||||||||
| 関連名称 | 10.1021/acs.joc.9b01933 | |||||||||||||
| 出版タイプ | ||||||||||||||
| 出版タイプ | AM | |||||||||||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||||||||||
| タイトル | ||||||||||||||
| タイトル | Palladium-Catalyzed Sequential Twofold Nucleophilic Substitution on 3-Bromopenta-2,4-dienyl Phosphate : Preparation of C1- and C2-Symmetric Doubly Functionalized Allenes | |||||||||||||
| 著者 |
Chen, Yen-Chou
× Chen, Yen-Chou
× 小笠原, 正道
WEKO
824
|
|||||||||||||
| 抄録 | ||||||||||||||
| 内容記述 | Readily available 3-bromopenta-2,4-dienyl esters (1x, acetate; 1y, benzoate; 1z, diethyl phosphate) were applied to the palladium-catalyzed reaction with various soft nucleophiles. The reaction proceeded through the twofold nucleophilic substitution via formal SN2'- and SN2-processes giving the various doubly functionalized allenes 2 in good yields. In the reactions of carboxylates 1x and 1y, the first substitution took place at the C-Br bond to form (allenyl)methyl ester intermediates 3. Because the second substitution on 3 proceeded faster than the first substitution on 1x or 1y, 3 were not isolable and C2-symmetric allenes 2 were obtained even in the presence of remaining 1x and 1y. On the other hand, the phosphate moiety was more reactive than the C-Br moiety in 1z. The initial products from 1z were 5-Nu-3-bromopenta-1,3-dienes 4 which were less reactive than 1z. Monosubstitution products 4 were isolable, and the stepwise introduction of two different Nu groups in C1-symmetric allenes 2 was realized starting with 1z under the controlled reaction conditions. By the use of a chiral palladium catalyst, axially chiral doubly functionalized allenes were obtained in up to 95% ee. | |||||||||||||
| 書誌情報 |
en : The Journal of Organic Chemistry 巻 84, 号 19, p. 12463-12470, 発行日 2019-09-09 |
|||||||||||||
| 収録物ID | ||||||||||||||
| 収録物識別子タイプ | ISSN | |||||||||||||
| 収録物識別子 | 00223263 | |||||||||||||
| 収録物ID | ||||||||||||||
| 収録物識別子タイプ | ISSN | |||||||||||||
| 収録物識別子 | 15206904 | |||||||||||||
| 収録物ID | ||||||||||||||
| 収録物識別子タイプ | NCID | |||||||||||||
| 収録物識別子 | AA00704100 | |||||||||||||
| 収録物ID | ||||||||||||||
| 収録物識別子タイプ | NCID | |||||||||||||
| 収録物識別子 | AA12097242 | |||||||||||||
| 出版者 | ||||||||||||||
| 出版者 | ACS Publications | |||||||||||||
| 権利情報 | ||||||||||||||
| 権利情報 | This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b01933. | |||||||||||||
| EID | ||||||||||||||
| 識別子 | 360018 | |||||||||||||
| 言語 | ||||||||||||||
| 言語 | eng | |||||||||||||
