An Efficient Method of Removing Chiral 2-Oxazolidinone Auxiliaries in a Methoxide-Carbonate System. Its Optimization and Synthetic Application
| Project/Area Number |
12650838
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
有機工業化学
|
|---|
| Research Institution | Meiji University |
|---|
Principal Investigator |
KANOMATA Nobuhiro Meiji Univ., Dept. of Industrial Chem., Associate Professor, 理工学部, 助教授 (40221890)
|
|---|
| Project Period (FY) |
2000 – 2001
|
| Project Status |
Completed (Fiscal Year 2001)
|
| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2001: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2000: ¥2,500,000 (Direct Cost: ¥2,500,000)
|
|---|
| Keywords | Chiral Auxiliary / Efficient Removal / N-Acyl-2-oxazolidinone / Methoxide Ion / Ester Synthesis / Hydroxyethylamide / Dimethyl Carbonate / ナトリウムメトキシド |
|---|
| Research Abstract |
We have accomplished the efficient N-acyl bond cleavage of both N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide based on the reaction with NaOMe in the presence of excess dimethyl carbonate to accomplish a clean removal of those chiral auxiliaries. These reactions generally proceed under mild conditions to give the corresponding methyl esters in high yields. The N-acyl bond cleavage described here are especially useful for sterically demanding molecules with quaternary carbons neighboring exocyclic or carbamoyl carbonyl of N-acyl-2-oxazolidinones or N-(2-hydroxyethyl)amides and for thermodynamically less stable molecules such as atropisomeric compounds with planar, axial, or herical chirality, which face a risk of isomerization at higher temperatures.
|
Report
(3 results)
Research Products
(8 results)
