| Item type |
デフォルトアイテムタイプ_（フル）(1) |
| 公開日 |
2023-03-18 |
| タイトル |
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|
タイトル |
Stereochemical Course of Deprotonation-Acylation of N-Boc- and N-Carbamoyl-2-cyano-6-methylpiperidines |
|
言語 |
en |
| 作成者 |
Kotomori, Yuri
Sasaki, Michiko
Kawahata, Masatoshi
Yamaguchi, Kentaro
Takeda, Kei
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| アクセス権 |
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|
アクセス権 |
open access |
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アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 権利情報 |
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|
権利情報 |
Copyright (c) 2015 American Chemical Society |
| 権利情報 |
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|
権利情報 |
This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
| 主題 |
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主題Scheme |
NDC |
|
主題 |
490 |
| 内容記述 |
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|
内容記述 |
The stereochemical course of electrophilic substitution of α-nitrile metallocarbanions generated by deprotonation from N-Boc- and N-carbamoyl-2-cyano-6-methylpiperidines was investigated. Deprotonation in the presence of an electrophile taking advantage of the high acidity of α-nitrile protons allowed examination of the effects of a chelating group on the nitrogen atom, a countercation, and the reactivity of an electrophile on the steric course. Analyses of reactions using aroyl chlorides and methyl iodide revealed the following: (1) the substitution reactions basically proceed with retention of configuration, (2) the extent of an inversion product increases with decreasing chelating ability of the N-substituent and with increasing leaving ability (ionic character) of a countercation (Li, Na, K) of the anionic species, and (3) the use of a more reactive electrophile results in an increase of the retention product. |
|
言語 |
en |
| 内容記述 |
|
|
内容記述タイプ |
Other |
|
内容記述 |
This research was partially supported by a Grant-in-Aid for Scientific Research (C) 25460015 (M.S.) a Grant-in-Aid for Scientific Research (B) 22390001 (K.T.), a Grant-in-Aid for Challenging Exploratory Research 23659007 (K.T.) and 15K14929 (K.T.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), the Hoansha Foundation (M.S.), the Takeda Science Foundation (M.S.) and the Naito Foundation Natural Science Scholarship (M.S.). |
| 出版者 |
|
|
出版者 |
American Chemical Society |
| 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 |
| 出版タイプ |
|
|
出版タイプ |
VoR |
|
出版タイプResource |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| 関連情報 |
|
|
関連タイプ |
isVersionOf |
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関連名称 |
http://doi.org/10.1021/acs.joc.5b02178 |
| 関連情報 |
|
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|
識別子タイプ |
DOI |
|
|
関連識別子 |
10.1021/acs.joc.5b02178 |
| 関連情報 |
|
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|
識別子タイプ |
PMID |
|
|
関連識別子 |
26457453 |
| 収録物識別子 |
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収録物識別子タイプ |
ISSN |
|
収録物識別子 |
0022-3263 |
| 開始ページ |
|
|
開始ページ |
11013 |
| 書誌情報 |
The Journal of Organic Chemistry
The Journal of Organic Chemistry
巻 80,
号 21,
p. 11013-11020,
発行日 2015-11-06
|
| 旧ID |
40588 |
JOrgChem_80_11013.pdf (965.6 KB)
