研究者業績

三野 孝

ミノ タカシ  (Takashi Mino)

基本情報

所属
千葉大学 大学院工学研究院 教授
(兼任)兼務
(兼任)兼務
学位
博士(工学)(同志社大学)

ORCID ID
 https://orcid.org/0000-0003-1588-1202
J-GLOBAL ID
200901055246875852
Researcher ID
F-8350-2010
researchmap会員ID
1000249453

外部リンク

論文

 231
  • Yasushi Yoshida, Hidetoshi Ida, Takashi Mino, Masami Sakamoto
    Molecules 28(11) 2023年6月  
    1,2,4-Triazole and 1,2,4-triazoline are important components of bioactive molecules and catalysts employed in organic synthesis. Therefore, the efficient synthesis of these components has received significant research attention. However, studies on their structural diversity remain lacking. Previously, we developed chiral phase-transfer-catalyzed asymmetric reactions of α-imino carbonyl compounds with α,β-unsaturated carbonyl compounds and haloalkanes. In this study, we demonstrate the formal [3 + 2] cycloaddition reaction of α-imino esters with azo compounds under Brønsted base catalysis, resulting in the corresponding 1,2,4-triazolines in high yields. The results revealed that a wide range of substrates and reactants can be applied, irrespective of their steric and electronic characteristics. The present reaction made the general preparation of 3-aryl pentasubstituted 1,2,4-triazolines possible for the first time. Furthermore, a mechanistic study suggested that the reaction proceeds without isomerization into the aldimine form.
  • Yasushi Yoshida, Naoyuki Aso, Takashi Karatsu, Takashi Mino, Masami Sakamoto
    Organic Letters 2023年5月8日  
  • Takashi Mino, Kaho Takaya, Kaito Koki, Natsume Akimoto, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
    Organic and Biomolecular Chemistry 2023年  
    We synthesized N-alkyl-N-cinnamoyl amide type phosphine-olefin compounds 1 and found axial chirality in a C(aryl)-N(amide) bond in compounds 1 by HPLC analysis using a chiral stationary phase column. We successfully obtained enantiomeric isomers of 1 and demonstrated the use of (-)-1 for chiral ligands in Pd-catalyzed asymmetric allylic substitution reactions of allylic esters with indoles (up to 97% ee).
  • Yasushi Yoshida, Tatsuya Ao, Takashi Mino, Masami Sakamoto
    MOLECULES 28(1) 2023年1月  
    There has been a great focus on halogen-bonding as a unique interaction between electron-deficient halogen atoms with Lewis basic moieties. Although the application of halogen-bonded atoms in organic chemistry has been eagerly researched in these decades, the development of chiral molecules with halogen-bonding functionalities and their utilization in asymmetric catalysis are still in the\ir infancy. We have previously developed chiral halonium salts with amide functionalities, which behaved as excellent catalysts albeit in only two reactions due to the lack of substrate activation abilities. In this manuscript, we have developed chiral halonium salts with an N-nitrosamine moiety and applied them to the Mannich reaction of isatin-derived ketimines with malonic esters. The study focused on our novel bromonium salt catalyst which provided the corresponding products in high yields with up to 80% ee. DFT calculations of the chiral catalyst structure suggested that the high asymmetric induction abilities of this catalyst are due to the Lewis basic role of the N-nitrosamine part. To the best of our knowledge, this is the first catalytic application of N-nitrosamines.

MISC

 125

書籍等出版物

 1

講演・口頭発表等

 108

担当経験のある科目(授業)

 16

共同研究・競争的資金等の研究課題

 8

社会貢献活動

 12