1995 Fiscal Year Final Research Report Summary
Synthesis and Reaction of Optically Active Heterocycles Containing Phosphorus Oxygen, and Sulfur
Project/Area Number |
06640706
|
Research Category |
Grant-in-Aid for General Scientific Research (C)
|
Allocation Type | Single-year Grants |
Research Field |
Organic chemistry
|
Research Institution | Fukuoka University |
Principal Investigator |
OKUMA Kentaro Fukuoka Univ., Fac.of Sciences, Associate Prof., 理学部, 助教授 (20131815)
|
Co-Investigator(Kenkyū-buntansha) |
OHTA Hiroshi Fukuoka Univ., Fac.of Sciences, Prof., 理学部, 教授 (60078574)
|
Project Period (FY) |
1994 – 1995
|
Keywords | Oxaphospholane / Thiaphospholane / Homoallylic Alcohol / Recifeiolide / Aldehyde / Paraformaldehyde / Optically Active / Witting Reaction |
Research Abstract |
The studies on the reaction of Witting reagents with epoxides have been done several researchers more than thirty years. In 1967, Hands and Mercer reported the first isolation of a 1,2lambda^5- oxaphospholane. Enholm and co-workers have reported the sequential Witting-oxyanion accelerated Core reaction of 2,2,2-triphenuyl-5-vinyl-1,2lambda^5-oxaphospholane, which was prepared by the reaction of butadiene monooxide with methylenetriphenylphosphorane. Thus, we tried the synthesis of optically active 1,2lambda^5-oxaphospholanes. Optically pure 1,2lambda^5-oxaphospholanes have been successfully prepared by the action of sodium hydride with optically active 3-hydroxyalkyltriphenylphosphonium salts. The reaction of 1,2lambda^5-oxaphospholanes with aldehydes afforded the corresponding homoallylic alcohols in nearly quantitative yields (E : Z=2 : 8). Recifeiolide, which is known as an macrocyclic lactone, was synthesized by five step reactions containing this key-step reactin. On the other hand, 1,2lambda^5-thiaphospholanes could not be isolated by the reaction of 3-mercaptopropyltriphenylphosphonium iodide with sodium hydride. Thus, we found that the reactivity between 3-hydroxyalkylphosphnium salts and 3-mercaptoalkylphoshonium salts was quite different.
|
Research Products
(9 results)
-
-
-
-
-
-
[Publications] Okuma, K., Miyazaki, K., Okumura, S., Tsujimoto, Y., Kojima, K., Ohta, H., &Yokomori, Y.: "A Novel Reactiton of Selenobenzophenones with Tetracyanoethylene. Formation of a 2,3-Dihydroselenophene." Tetrahedron Lett.36. 8813-8816 (1995)
Description
「研究成果報告書概要(欧文)」より
-
[Publications] Okuma, K., Sato, Y., Kuge, S., Ikari, K., Ono, M., Ohta, H., &Machiguchi, T.: "Reaction of Vinylphosphonium Salts with Sulfoxonium Ylides. Synthesis of Cyclopropylphosphonium Salts." Bull, Chem.Soc.Jpn.68. 2313-2317 (1995)
Description
「研究成果報告書概要(欧文)」より
-
-