このアイテムのアクセス数: 13

このアイテムのファイル:
ファイル 記述 サイズフォーマット 
s41467-017-01099-x.pdf742.22 kBAdobe PDF見る/開く
タイトル: Organocatalytic enantio- and diastereoselective cycloetherification via dynamic kinetic resolution of chiral cyanohydrins
著者: Yoneda, Naoki
Fujii, Yuki
Matsumoto, Akira
Asano, Keisuke
Matsubara, Seijiro
著者名の別形: 米田, 直紀
藤井, 結稀
松本, 晃
浅野, 圭佑
松原, 誠二郎
キーワード: Drug development
Drug discovery and development
Organocatalysis
Stereochemistry
発行日: 9-Nov-2017
出版者: Springer Nature
誌名: Nature Communications
巻: 8
論文番号: 1397
抄録: Enantioselective approaches to synthesize six-membered oxacycles with multiple stereogenic centres are in high demand to enable the discovery of new therapeutic agents. Here we present a concise organocatalytic cycloetherification for the highly enantio- and diastereoselective synthesis of tetrahydropyrans involving simultaneous construction of two chiral centres, one of which is fully substituted. This method involves dynamic kinetic resolution of reversibly generated chiral cyanohydrins. A chiral bifunctional organocatalyst selectively recognizes a specific chair-like conformation of the intermediate, in which the small steric effect of the linear cyano group as well as its anomeric effect play important roles in controlling stereoselectivity. The products offer additional utility as synthetic intermediates because the cyano group can be further transformed into a variety of important functional groups. This strategy provides a platform to design efficient approaches to obtain a wide range of optically active tetrahydropyrans, which are otherwise synthetically challenging materials.
記述: 特定の分子にのみ反応する酵素の特徴を応用し精密有機合成を実現 --薬剤候補物質の効率的な合成へ--. 京都大学プレスリリース. 2017-11-14.
著作権等: © The Author(s) 2017. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
URI: http://hdl.handle.net/2433/227881
DOI(出版社版): 10.1038/s41467-017-01099-x
関連リンク: http://www.kyoto-u.ac.jp/ja/research/research_results/2017/171110_1.html
出現コレクション:学術雑誌掲載論文等

アイテムの詳細レコードを表示する

Export to RefWorks


出力フォーマット 


このリポジトリに保管されているアイテムはすべて著作権により保護されています。