2013 Fiscal Year Final Research Report
Synthesis and Application of New Compounds with Both Axial and Helical Chiralities
| Project/Area Number |
23350021
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Kyushu University |
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Principal Investigator |
INANAGA Junji 九州大学, 先導物質化学研究所, 学術研究員 (50091244)
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| Co-Investigator(Kenkyū-buntansha) |
ONITSUKA Satoaki 鹿児島大学, 大学院・理工学研究科, 助手 (60403937)
FURUNO Hiroshi 九州大学, グリーンアジア国際リーダー教育センター, 准教授 (90335993)
ISHIZUKA Kentaro 九州大学, 先導物質化学研究所, 学術研究員 (20531578)
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| Project Period (FY) |
2011-04-01 – 2014-03-31
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| Keywords | 合成有機化学 / 分子認識 / 構造有機化学 / 光学活性オリゴマー / 多機能触媒 |
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| Research Abstract |
We succeeded in synthesizing 1,1'-bi-2-naphthol (BINOL) oligomers (dimer~octamer), which are directly connected at the 3,3'-positions of (R)-BINOL, in pure states and in good overall yields. The dimer was found to work as an excellent NMR shift reagent for chiral sulfoxides. The corresponding mono-calcium complex and low-valent dinuclear Ti-complex were found to work as a chiral bifunctional catalyst for the Michael reaction of nitromethane and to be effective for the pinacol coupling reaction, respectively, in which induced-fit-type reactions are anticipated. The trimer caused interestingly unique helical assembly of water molecules thus leading to the formation of chiral single strand water wire. It was found that the dynamic chirality of oligoBINOLs could be controlled by external stimuli such as pH. The UV-VIS and CD spectra of oligoBINOLs showed unusual trend on the pentamer indicating the formation of a unispiral structure.
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