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 |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | Shibaura Institute of Technology |
Principal Investigator |
|
Project Period (FY) |
2014-04-01 – 2017-03-31
|
Project Status |
Completed (Fiscal Year 2016)
|
Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
|
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 / エナンチマー / エナンチオ選択性 / エナンチオ選択的 / ルイス酸 |
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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Report
(4 results)
Research Products
(9 results)