2013 Fiscal Year Final Research Report
Studies on synthesis of heterocycles and carbocycles by sequential reactions using unsaturated esters
| Project/Area Number |
23550054
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Research Field |
Organic chemistry
|
|---|
| Research Institution | Nara University of Education |
|---|
Principal Investigator |
|
|---|
| Project Period (FY) |
2011 – 2013
|
| Keywords | 合成反応 / 効率的結合形成 / ルイス酸 / 不飽和エステル |
|---|
| Research Abstract |
New efficient cyclization reactions using highly reactive alfa,beta-unsaturated esters by sequential bond formations has been developed.
The reaction of unsaturated esters such as ethenetricarboxylates, 2-phosphonoacrylate and 2-(trifluoromethyl)acrylate with diethyl azodicarboxylate and PPh3 gave pyrazolines efficiently. Reaction of allyl ethenetricarboxylates and the amides with Lewis acids such as TiCl4, TiBr4 and AlCl3 gave 3,4-trans-halogenomethyl 2-oxotetrahydrofuran and pyrrolidine derivatives stereoselectively in high yields. The stereochemistries were determined by NOE experiments. Reaction of (E)/(Z)-2-butenyl esters with AlCl3 or FeCl3 gave 3,4-trans 4-(1-chloroethyl) tetrahydro-2-oxofuran diastereoisomers stereospecifically. Reaction of (E)/(Z)-2-butenyl and 2-pentenyl amides with ZnI2 gave 3,4-trans 4-(1-iodoethyl and propyl) tetrahydro-2-oxopyrrolidine diastereoisomers stereospecifically.
These reactions represent efficient ways to construct potentially useful compounds.
|
Research Products
(30 results)
