Design of novel chirality of macrocyclic compound bearing heteroaromatic biaryls

带有杂芳联芳基的大环化合物的新型手性设计

• 批准号: 24655083
• 负责人: MORI Atsunori
• 金额: $ 2.66万
• 依托单位: Kobe University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Challenging Exploratory Research
• 财政年份: 2012
• 资助国家: 日本
• 起止时间: 2012-04-01 至 2014-03-31
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-24655083/
• 关键词: 分子不斉; ヘテロ芳香族; キラルHPLC; CHホモカップリング; 閉環メタセシス; イミダゾール; チオフェン; X線結晶構造解析; ヘテロビアリール; 軸性不斉; ルテニウム触媒; 光学分割; ビスアゾール

Design of winding-vine-shaped organic molecule was carried out. The obtained compound was found to show molecular asymmetry, which is a molecule with no carbogenic chiral center. Imidazole derivatives as a nitrogen-containing heteroaromatic compound was subjected to CH homocoupling reaction and following ruthenium-catalyzed ring-closing metathesis leading to the compounds showing molecular asymmetry. The structure of the obtained molecule was confirmed by X-ray structure analysis and its chirality was revealed by HPLC analysis with a chiral column. Separation of both enantiomers were also achievled by the resolution with a preparative chiral column. The related compound of molecular asymmetry was also prepared with a thiophene derivative, which was a heteroaromatic compound bearing a sulfur atom.

进行了缠绕藤状有机分子的设计。发现所获得的化合物显示分子不对称性，这是一个没有碳手性中心的分子。咪唑衍生物作为一种含氮芳香杂环化合物，经过CH同偶联反应和在铼催化下的关环复分解反应，导致化合物表现出分子的不对称性。所得分子的结构通过X射线结构分析确认，其手性通过使用手性柱的HPLC分析揭示。两种对映体的分离也通过制备型手性柱的拆分进行了验证。分子不对称性的相关化合物也用噻吩衍生物制备，噻吩衍生物是带有硫原子的杂芳族化合物。

项目成果

Axially Chiral Macrocyclic E-Alkene Bearing Bisazole Component Formed by Sequential C-H Homocoupling and Ring-Closing Metathesis

• DOI: 10.1021/ol300755y
• 发表时间: 2012-05-18
• 期刊: ORGANIC LETTERS
• 影响因子: 5.2
• 作者: Nishio, Shotaro;Somete, Takashi;Mori, Atsunori
• 通讯作者: Mori, Atsunori

軸性不斉イミダゾール骨格を有する大環状化合物の合成

轴不对称咪唑骨架大环化合物的合成

• 发表时间: 2013
• 作者: Shotaro Nishio;Takashi Somete;Atsushi Sugie;Tohru Kobayashi;Tsuyoshi Yaita;Atsunori Mori;Shotaro Nishio;Shinobu Mitsuda;森敦紀;岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀
• 通讯作者: 岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀

軸性不斉ビチオフェン骨格を有する大環状化合物の合成

轴不对称联噻吩骨架大环化合物的合成

• 发表时间: 2013
• 作者: Shotaro Nishio;Takashi Somete;Atsushi Sugie;Tohru Kobayashi;Tsuyoshi Yaita;Atsunori Mori;Shotaro Nishio;Shinobu Mitsuda;森敦紀;岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀;辻悟,光田紫乃布,岡山陽一,杉江敦司,小林徹,宮崎有史,矢板毅,森敦紀
• 通讯作者: 辻悟,光田紫乃布,岡山陽一,杉江敦司,小林徹,宮崎有史,矢板毅,森敦紀

Synthesis and Properties of Regioregular Poly(3-substituted thiophene) Bearing Disiloxane Moiety in the Substituent. Remarkably High Solubility in Hexane

• DOI: 10.1246/cl.131222
• 发表时间: 2014-01
• 期刊: Chemistry Letters
• 影响因子: 1.6
• 作者: A. Mori;Kenji Ide;Shunsuke Tamba;S. Tsuji;Y. Toyomori;T. Yasuda

ヘテロ芳香族化合物のCHカップリング反応新反応開発から応用まで

杂芳烃CH偶联反应从新反应开发到应用

• 发表时间: 2013
• 作者: Shotaro Nishio;Takashi Somete;Atsushi Sugie;Tohru Kobayashi;Tsuyoshi Yaita;Atsunori Mori;Shotaro Nishio;Shinobu Mitsuda;森敦紀
• 通讯作者: 森敦紀