New Approach for Complete Reversal of Enantioselectivity Using a Single Chiral Source
| Project/Area Number |
17350020
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (B)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Organic chemistry
|
|---|
| Research Institution | Kobe University |
|---|
Principal Investigator |
HAYASHI Masahiko Kobe University, Department of Chemistry, Graduate School of Science, Professor (60192704)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
AMII Hideki Kobe University, Department of Chemistry Graduate School of Science, Associate Professor (00284084)
|
|---|
| Project Period (FY) |
2005 – 2007
|
| Project Status |
Completed (Fiscal Year 2007)
|
| Budget Amount *help |
¥15,530,000 (Direct Cost: ¥15,200,000、Indirect Cost: ¥330,000)
Fiscal Year 2007: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2006: ¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 2005: ¥11,700,000 (Direct Cost: ¥11,700,000)
|
|---|
| Keywords | asymmetric synthesis / enantioselective reaction / chiral ligand / Schiff base / Oxazoline / carbon-carbon bond formation / aldimine / ketoimine / 鏡像体 / 光学純度 / 不斉アルキル化 / 光学活性 / 不斉触媒 |
|---|
| Research Abstract |
Attempt for obtaining both enantiomers in high enantiomeric excess is attractive and important challenges, because it is often the case that each enantiomer exhibits different bioactivity. This review summarizes some approaches to realize complete reversal of enantioselectivity by changing various conditions. Our new approach to achieve reversal of enantioselection in the reaction of enantioselective addition of diketene to aldehydes affording optically active 5-hydroxy-3-ketoesters in high optical yield using Schiff bases containing oxazoline moiety derived from L-serine, was achieved. Starting from one chiral center (in this case from L-serine), we obtained two chiral Schiff base possessing oxazoline moieties, each of which recognized different enantioface of aldehydes in the addition reaction of diketene to aldehydes in high level (up to 93% ee R and 89% ee (S), respectively). This is the first example of complete reversal of enantioselection from the single chirality of L-serine.
|
Report
(4 results)
Research Products
(27 results)
