| Item type |
文献 / Documents(1) |
| 公開日 |
2025-03-28 |
| アクセス権 |
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|
アクセス権 |
open access |
|
アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 資源タイプ |
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|
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/10.1055/a-2347-1027 |
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|
関連名称 |
10.1055/a-2347-1027 |
| 出版タイプ |
|
|
出版タイプ |
VoR |
|
出版タイプResource |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| タイトル |
|
|
タイトル |
Synthesis of Methyl 2-[Bis(benzylthio)phosphoryl]acetate as a Novel Horner–Wadsworth–Emmons-Type Reagent and Its Application to the Diastereodivergent Synthesis of (E)- and (Z)-α,β-Unsaturated Esters |
| 著者 |
佐野, 茂樹
Yamada, Shoki
Ihara, Takahito
Seki, Kazumasa
北池, 秀次
中尾, 允泰
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| 抄録 |
|
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内容記述 |
Methyl 2-[bis(benzylthio)phosphoryl]acetate has proven to be an efficient Horner–Wadsworth–Emmons (HWE)-type reagent for the diastereodivergent synthesis of (E)- and (Z)-α,β-unsaturated esters. Under the conditions of excess NaHMDS relative to the HWE-type reagent, the HWE-type reactions of methyl 2-[bis(benzylthio)phosphoryl]acetate with various aldehydes afforded the corresponding α,β-unsaturated esters in an E-selective manner in up to 100:0 E/Z ratio. However, when an excess of the HWE-type reagent was used relative to NaHMDS, the stereoselectivity of the HWE-type reactions was dramatically changed from E to Z, yielding an E/Z ratio of up to 2:98. |
| キーワード |
|
|
主題 |
Horner–Wadsworth–Emmons reagent |
| キーワード |
|
|
主題 |
phosphorus–sulfur bond |
| キーワード |
|
|
主題 |
α,β-unsaturated esters |
| キーワード |
|
|
主題 |
diastereodivergent synthesis |
| キーワード |
|
|
主題 |
olefination |
| キーワード |
|
|
主題 |
aldehydes |
| 書誌情報 |
en : Synlett
巻 36,
号 5,
p. 546-550,
発行日 2024-07-03
|
| 収録物ID |
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|
収録物識別子タイプ |
PISSN |
|
収録物識別子 |
09365214 |
| 収録物ID |
|
|
収録物識別子タイプ |
EISSN |
|
収録物識別子 |
14372096 |
| 収録物ID |
|
|
収録物識別子タイプ |
NCID |
|
収録物識別子 |
AA10731110 |
| 出版者 |
|
|
出版者 |
Georg Thieme Verlag |
| 権利情報 |
|
|
権利情報 |
This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/) |
| EID |
|
|
識別子 |
416737 |
| 言語 |
|
|
言語 |
eng |
synlett_36_5_546.pdf (438 KB)
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