2013 Fiscal Year Final Research Report
Development of construction of multi-chiral center by one reaction ising meso trick
| Project/Area Number |
23350043
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (B)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Synthetic chemistry
|
|---|
| Research Institution | Kobe University |
|---|
Principal Investigator |
HAYASHI MASAHIKO 神戸大学, 理学(系)研究科(研究院), 教授 (60192704)
|
|---|
| Project Period (FY) |
2011-04-01 – 2014-03-31
|
| Keywords | メソ化合物 / 光学活性シッフ塩基 / 光学活性トリオール / オキシピリン類 / オゾン酸化 |
|---|
| Research Abstract |
Treatment of 4,5-epoxycyclohex-1-ene with ter-butylperbenzoic acid in the presence of Cu (I)-chiral N,N-bidente complex gave the (3S,4S,5S)-3-benzoyloxy-4-epoxycyclohexa-1-en in 54% chemical yield and 84% ee. The ee of this compound could be increased up to 100% ee by recrystalization after derivatization to the corresponding p-nitrobenzoyl derivative.
ring opening of the product epoxide with H2O followed by ozonolysis afforded the acyclic chiral triol. this method is useful for the synthesis of natural product such as oxylipines.
|
