2009 Fiscal Year Final Research Report
Efficient Syntheses of Highly Substituted Organic Molecules Starting from Torquoselective Olefination
| Project/Area Number |
19390007
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (B)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Kyushu University |
|---|
Principal Investigator |
SHINDO Mitsuru Kyushu University, 先導物質化学研究所, 教授 (40226345)
|
|---|
| Project Period (FY) |
2007 – 2009
|
| Keywords | 有機合成化学 / オレフィン化反応 / 電子環状反応 / 理論計算 / 立体電子効果 / 不斉触媒 / マイクロリアクター |
|---|
| Research Abstract |
We have developed the highly stereoselective olefination of carbonyl compounds with ynolates, and clarified the reaction mechanism by the theoretical calculations and the generality. The olefination of alkynyl ketones via ynolates provided the corresponding en-yne compounds with high E-selectivity, in which the alkynyl group works as an electron donating group in the torquoselectivity. The resulting olefins were converted into β-alkoxy divinyl ketones, which was subjected to the catalytic Nazarov reaction to afford α-alkoxy cyclopentenones in good yield. This cyclization was applied to the synthetic study of stemona alkaloids.
|
