Asymmetric Hydroarylation of Alkynes Based on the Formation of Vinylidene ortho-Quinone Methides
| Project/Area Number |
17K05788
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Kumamoto University |
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Principal Investigator |
Ryo Irie 熊本大学, 大学院先端科学研究部(理), 教授 (70243889)
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| Project Period (FY) |
2017-04-01 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | 不斉合成 / 有機触媒 / 塩基触媒 / アルキン / ヒドロアリール化 / 分子内環化 / 軸不斉化合物 / 螺旋不斉化合物 / 環化 / ヘテロビアリール / 触媒的不斉合成 / 軸不斉 / 螺旋不斉 |
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| Outline of Final Research Achievements |
Introduction of axial and helical chirality to carbazoles (CBZ), which have remarkable electro and photo properties, may lead to characteristic chiral functional materials. To this end, we have developed catalytic asymmetric hydroarylation of linked alkyne-indole systems and thereby, achieved the synthesis of CBZ-biaryl derivatives with axial chirality in high optical purity. Furthermore, transformation of the CBZ bialys thus obtained to heterohelicenes was examined to permit successful asymmetric synthesis of CBZ-helicenes with both helical and axial chirality.
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| Academic Significance and Societal Importance of the Research Achievements |
アルキンの不斉ヒドロアリール化反応は未だに例が極めて限られており，しかも従来法のほとんどがパラジウムや金などの貴金属触媒に基づいている．これに対して，本研究では，安価な有機触媒を用いるアルキンの不斉ヒドロアリール化の開発に世界に先駆けて成功した．その斬新な反応機構や立体化学経路も明らかにすることができた．本反応によって得られる光学活性な化合物は他法では得難く，キラルな機能性分子材料としての応用研究への展開が期待される．
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Report
(4 results)
Research Products
(18 results)
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[Journal Article] Synthesis and stereochemical properties of chiral hetero[7]helicenes structured by a benzodiheterole ring core2017
Author(s)
Sachie Arae, Takaaki Mori, Takahiro Kawatsu, Daiki Ueda, Yusuke Shigeta, Nobutsugu Hamamoto, Hitoshi Fujimoto, Michinori Sumimoto, Tatsushi Imahori, Kazunobu Igawa, Katsuhiko Tomooka, Tharmalingam Punniyamurthy, Ryo Irie
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Journal Title
Chemistry Letters
Volume: 46
Issue: 8
Pages: 1214-1216
DOI
NAID
Related Report
Peer Reviewed / Open Access / Int'l Joint Research
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