1, 3-双極子を活用する複素環合成の革新

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Author: 宇梶, 裕ほか

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Publication date: 2016-06-13

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Note (General)：: 金沢大学理工学域物質科学系医薬，農薬においては複素環は重要な役割を果たすことから，新規医薬，農薬など高付加価値物質の創生には複素環合成の新手法開拓が必須である。本研究では，窒素，酸素などのヘテロ原子を有してアトムエコノミカルな複素環合成に有効な1,3-双極子を活用し，「協奏的1,3-双極子付加環化の...

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https://kaken.nii.ac.jp/report/KAKENHI-PROJECT-24350022/24350022seika/

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Material Type: 文書・図像類
Title: 1, 3-双極子を活用する複素環合成の革新
Author/Editor: 宇梶, 裕
Ukaji, Yutaka
Author Heading: 宇梶, 裕
Ukaji, Yutaka
Publication Date: 2016-06-13
Publication Date (W3CDTF): 2016-06-13
Alternative Title: Innovation in Synthesis of Heterocycles Utilizing 1,3-Dipoles
Periodical title: 平成27(2015)年度科学研究費補助金基盤研究(B) 研究成果報告書 = 2015 Fiscal Year Final Research Report
No. or year of volume/issue: 2012-04-01 – 2016-03-31
Volume: 2012-04-01 – 2016-03-31
Pages: 6p.-
Text Language Code: jpn
Subject Heading: 1,3-双極子
複素環
協奏的付加環化
段階的付加－環化
共役拡張型1,3-双極子
1,5-双極子
光学活性
Target Audience: 一般
Note (General): 金沢大学理工学域物質科学系
医薬，農薬においては複素環は重要な役割を果たすことから，新規医薬，農薬など高付加価値物質の創生には複素環合成の新手法開拓が必須である。本研究では，窒素，酸素などのヘテロ原子を有してアトムエコノミカルな複素環合成に有効な1,3-双極子を活用し，「協奏的1,3-双極子付加環化の力量化」としてアゾメチンイミンの不斉1,3-双極子付加環化反応，「段階的（＝非協奏的）付加－環化を基盤とする集積反応系の確立」として，ニトロンへの不斉求核付加-環化反応，および「1,5-双極子のルネサンス」として，C,N-環状N’-アシルアゾメチンイミンの〔5+1〕環化反応など，３つの方向から複素環合成の革新を実現した。
The development of a practical and efficient method for construction of heterocycles is an essential part of programs to explore new medical and agrochemical agents. 1,3-Dipoles are important chemical species containing heteroatoms. We studied on innovative syntheses heterocycles utilizing 1,3-dipoles based on three strategies.We designed a novel chiral reaction system possessing multi-metal centers utilizing tartaric acid ester as a chiral auxiliary. Based on this concept, we developed asymmetric 1,3-dipolar cycloadditions of azomethine imines to allylic alcohols. A strategy consisted of a stepwise addition to 1,3-dipoles, followed by cyclizaion was found to be an alternative and regiocontrolled pathway to synthesize of heterocycles. An asymmetric addition of acetylides to nitrones followed by cyclization was developed to give the corresponding optically active 4-isoxazolines. A novel [5+1] cycloaddition reaction of N’-acyl azomethine imines with isocyanides was also explored.
研究課題/領域番号:24350022, 研究期間(年度):2012-04-01 – 2016-03-31
DOI: 10.24517/00034431
Source: https://kanazawa-u.repo.nii.ac.jp/?action=repository_action_common_download&item_id=34444&item_no=1&attribute_id=26&file_no=1
https://kanazawa-u.repo.nii.ac.jp/?action=repository_action_common_download&item_id=34444&item_no=1&attribute_id=26&file_no=1
Access Restrictions: 限定公開
Rights (production): CC BY-NC-ND
Related Material: https://kaken.nii.ac.jp/search/?qm=80193853
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-24350022/
https://kaken.nii.ac.jp/report/KAKENHI-PROJECT-24350022/24350022seika/
Data Provider (Database): 国立情報学研究所 : 学術機関リポジトリデータベース（IRDB）（機関リポジトリ）
https://irdb.nii.ac.jp
Original Data Provider (Database): 金沢大学 : 金沢大学学術情報リポジトリKURA