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Tris(pentafluorophenyl)borane‐Assisted Chiral Phosphoric Acid Catalysts for Enantioselective Inverse‐Electron‐Demand Hetero‐Diels‐Alder Reaction of α,β‐Substituted Acroleins
http://hdl.handle.net/2237/00030882
http://hdl.handle.net/2237/000308821a5fe20c-97a8-4dea-856f-3e6ae9107b95
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
Manuscript (1.3 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2019-11-14 | |||||
| タイトル | ||||||
| タイトル | Tris(pentafluorophenyl)borane‐Assisted Chiral Phosphoric Acid Catalysts for Enantioselective Inverse‐Electron‐Demand Hetero‐Diels‐Alder Reaction of α,β‐Substituted Acroleins | |||||
| 言語 | en | |||||
| 著者 |
Hatano, Manabu
× Hatano, Manabu× Sakamoto, Tatsuhiro× Mochizuki, Takuya× Ishihara, Kazuaki |
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| 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 | |||||
| 権利 | ||||||
| 言語 | en | |||||
| 権利情報 | This is the peer reviewed version of the following article: [M. Hatano, T. Sakamoto, T. Mochizuki, K. Ishihara, Asian J. Org. Chem. 2019, 8, 1061.], which has been published in final form at [https://doi.org/10.1002/ajoc.201900104]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | [4+2] cycloaddition | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | boron Lewis acid | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | chiral Brønsted acid catalyst | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | inverse-electron-demand hetero-Diels-Alder reaction | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | phosphoric acid | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | In the enantioselective inverse‐electron‐demand hetero‐Diels‐Alder reaction, simple α,β‐unsaturated aldehydes (i. e., acroleins) are still challenging substrates, unlike α,β‐unsaturated carbonyl compounds containing electron‐withdrawing groups. In the present study, the reaction of α‐aryl‐β‐alkyl‐substituted acroleins with ethyl vinyl sulfide was developed with the use of bulky chiral supramolecular Brønsted acid catalysts, such as tris(pentafluorophenyl)borane‐assisted chiral phosphoric acid catalysts. As a result, cis‐cycloadducts as optically active 3,4‐dihydro‐2H‐pyrans were exclusively obtained in high yields with high enantioselectivities via the favored endo orbital approach. An obtained optically active cis‐isomer could be transformed into the corresponding trans‐isomer without a loss of enantiopurity by O,S‐acetal epimerization. Moreover, transformations to synthetically useful optically active epoxide and δ‐valerolactone are also demonstrated. | |||||
| 言語 | en | |||||
| 内容記述 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | ファイル公開：2020/07/01 | |||||
| 言語 | ja | |||||
| 出版者 | ||||||
| 出版者 | Wiley | |||||
| 言語 | en | |||||
| 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 | AM | |||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
| DOI | ||||||
| 関連タイプ | isVersionOf | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | https://doi.org/10.1002/ajoc.201900104 | |||||
| ISSN（print） | ||||||
| 収録物識別子タイプ | PISSN | |||||
| 収録物識別子 | 2193-5807 | |||||
| 書誌情報 |
en : Asian Journal of Organic Chemistry 巻 8, 号 7, p. 1061-1066, 発行日 2019-07 |
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| 著者版フラグ | ||||||
| 値 | author | |||||
