1994 Fiscal Year Final Research Report Summary
Development of Carbonylative Generation of Ketene and Its Application to the Synthesis of Useful Compounds
| Project/Area Number |
05650859
|
|---|
| Research Category |
Grant-in-Aid for General Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Research Field |
有機工業化学
|
|---|
| Research Institution | Okayama University |
|---|
Principal Investigator |
OKUMOTO Hiroshi Okayama University, Graduate School of Natural Science and Technology, Research Associate, 大学院・自然科学研究科, 助手 (90183251)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
TANAKA Hideo Okayama University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (60032950)
|
|---|
| Project Period (FY) |
1993 – 1994
|
| Keywords | Carbonylation / allyl Phosphate / Palladium Catalyst / Ketene / Imine / beta-Lactam / Stereoselective Synthesis / 立体選択的反応 |
|---|
| Research Abstract |
A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited. Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (30Kgcm^<-2>) stereoselectively gave either a cis-or trans-3-alkeny1-beta-lactam in high yield. The stereochemical outcome strongly depends on the nature of the imine employed. Imines conjugated with a carbonyl such as a ketone or an ester stereoselectively produce cis-beta-lactams at room temperature, whereas imines unconjugated with a carbonyl group exclusively afford trans-beta-lactams at 70ﾟC.
|
