2016 Fiscal Year Final Research Report
Synthesis of optically active N-C axially chiral amines through enantioselective isomerization
| Project/Area Number |
26460014
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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 |
Chemical pharmacy
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| Research Institution | Shibaura Institute of Technology |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | 軸不斉 / アミン / 回転障壁 / プロトン酸 / エナンチオマー / 異性化 |
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| Outline of Final Research Achievements |
We succeeded in the synthesis of optically active N-C axially chiral amines and found their notable structural property. The addition of protic acid to N-C axially chiral cyclic amine brought about significant increase in the rotation rate around the chiral axis due to the formation of the protonated amine (Proton accelerator). On the other hand, N-C axially chiral amines, which result in the decrease in the rotation rate around the chiral axis by the addition of protic acid, was also found (Proton brake). Furthermore, we elucidated the mechanism of Proton accelerator and Proton brake through X-ray crystal structural analysis and DFT calculation.
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| Free Research Field |
有機化学
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