1988 Fiscal Year Final Research Report Summary
Research Aimed for the Development of Transition Metal Catalyzed Heterocyclic Synthesis.
| Project/Area Number |
61470094
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kyoto University |
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Principal Investigator |
TAMARU Yoshinao Faculty of Engineering, Kyoto University Professor, 工学部, 助教授 (80026319)
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| Co-Investigator(Kenkyū-buntansha) |
YOSHIDA Zen-ichi Faculty of Engineering, Kyoto University, Professor, 工学部, 教授 (60025814)
MIKI Sadao Faculty of Engineering, Kyoto University, Instructor, 工学部, 助手 (30135537)
SUGIMOTO Toyonari Faculty of Engineering, Kyoto University, Associate Professor, 工学部, 助手 (30093256)
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| Project Period (FY) |
1986 – 1988
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| Keywords | Oxidizing Potential of Pd(11) / Catalytic Reaction / Heterocycles / Urea Nucleophile / Dihydrouracil / αーメチレンーγーブチロラクトン |
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| Research Abstract |
This research was aimed to develop new synthetic methodologies for nitrogen and oxygen heterocycles by the use of the oxidizing potential of transition metals. The results obtained in these 3 years are summarized as follows.
(1) For the palladium(II) catalyzed amination of olefins, urea serves as a specific aminonucleophile (not an oxygen nucleophile) and shows the higher reactivity and versatility as compared with sulfonamide and carbamate, commonly utilized hitherto. Based on this methodology, the following classes of compounds can be synthesized very efficiently; cis 3-hydroxypyrrolidine-2-acetic acid lactones (versatile synthetic intermediates for pyrrolitidine alkaloid), bicyclic dihydrouracil, cyclic urea, gamm- and -amino amino acids. (2)alpha-Methylene-gamma-butyrolactones are synthesized by palladium(II) catalyzed carbonylation of 3-butyn-1-ols. The yields are highly dependent on the kind of bases. Propylene oxide proved to be the best base. (3) 2-Arylheterocycles (e.g., 2-aryltetrahydrofurans, 2-Arylpiperidines) are synthesized by the Pd(II)-catalyzed reaction of homoallyl alcohols and homoallylamines, respectively, with aryltrialkyltin.
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Research Products
(11 results)
