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  1. B200 工学部/工学研究科
  2. B200a 雑誌掲載論文
  3. 学術雑誌

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/2237/00030882
1a5fe20c-97a8-4dea-856f-3e6ae9107b95
名前 / ファイル ライセンス アクション
Manuscript.pdf Manuscript (1.3 MB)
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

WEKO 94187

en Hatano, Manabu

Search repository
Sakamoto, Tatsuhiro

× Sakamoto, Tatsuhiro

WEKO 94188

en Sakamoto, Tatsuhiro

Search repository
Mochizuki, Takuya

× Mochizuki, Takuya

WEKO 94189

en Mochizuki, Takuya

Search repository
Ishihara, Kazuaki

× Ishihara, Kazuaki

WEKO 94190

en Ishihara, Kazuaki

Search repository
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 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
内容記述タイプ Abstract
内容記述
内容記述 ファイル公開:2020/07/01
言語 ja
内容記述タイプ Other
出版者
言語 en
出版者 Wiley
言語
言語 eng
資源タイプ
資源タイプresource http://purl.org/coar/resource_type/c_6501
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
著者版フラグ
値 author
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