| Project/Area Number |
24655089
|
|---|
| Research Category |
Grant-in-Aid for Challenging Exploratory Research
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
Synthetic chemistry
|
|---|
| Research Institution | Waseda University |
|---|
Principal Investigator |
|
|---|
| Co-Investigator(Renkei-kenkyūsha) |
OGAWA Narihito 東京工業大学, 大学院生命理工学研究科, 助教 (50611109)
|
|---|
| Project Period (FY) |
2012-04-01 – 2014-03-31
|
| Project Status |
Completed (Fiscal Year 2013)
|
| Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2012: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
|
|---|
| Keywords | 熱力学制御 / 異性化晶出 / 異性化吸着 / 面不斉 / アザスピレン / ピリジノファン / ラセミ化 / 光学分割 / キラリティー / 立体制御 / スピロ骨格 / 異性化反応 |
|---|
| Research Abstract |
We have investigated isomerization properties of [14]parapyridinophane derivatives and demonstrated that crystallization-induced and adsorption-induced asymmetric transformations are efficient protocols to prefer the opposite sense of stereochemistry in planar-chiral [14]parapyridinophane derivatives, respectively. We have also found that azaspirene analog having its characteristic spiro skeleton readily undergoes racemization in neutral aqueous media and that efficient resolution was achieved by using an appropriate chiral auxiliary to resolve the analog by the following acidic hydrolysis of each diastereoisomer to afford highly enantio-enriched azaspirene analog in excellent yields without a loss of their enantiomeric excesses. The sequential transformation to enantiomerically pure analog and its recycling process to its racemic body achieved an efficient synthetic route to an optically active analog of azaspirene.
|
