2009 Fiscal Year Final Research Report
Development of Combo Metal Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols and Its Application to Efficient Transformations
| Project/Area Number |
20790015
|
|---|
| Research Category |
Grant-in-Aid for Young Scientists (B)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | University of Shizuoka |
|---|
Principal Investigator |
EGI Masahiro University of Shizuoka, 薬学部, 講師 (80363901)
|
|---|
| Project Period (FY) |
2008 – 2009
|
| Keywords | 複合触媒 / 転位反応 / 連続反応 / 固定化触媒 / 環境調和 |
|---|
| Research Abstract |
I have disclosed that the combination of MoO2(acac)2, (Ph3P)AuCl, and AgOTf provides a powerful catalytic system for the rapid 1,3-rearrangement of propargyl alcohols. The reactions proceed at room temperature within 1 h in most cases to afford a variety of α,β-unsaturated carbonyl compounds in excellent yields. During the further study on its application to various substrates, it was found that the cationic gold-catalyzed intramolecular cyclizations of the propargyl alcohols having carbonyl, hydroxyl, or amino groups gave the heterocyclic compounds, such as 3(2H)-furanones, furanes, and pyrroles. A polymer-supported cationic gold compound was also synthesized and showed high reactivity. It was recovered quantitatively from the reaction mixture by simple filtration and reused for four runs.
|
