1999 Fiscal Year Final Research Report Summary
Development of New Photo-, Electric-, and Molecular-Devised Materials Using High Pressure Technology
| Project/Area Number |
09554047
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
物質変換
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| Research Institution | Kochi University |
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Principal Investigator |
KOTSUKI Hiyoshizo Kochi University, Faculty of Science, Department of Chemistry, Professor, 理学部, 教授 (80093954)
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| Co-Investigator(Kenkyū-buntansha) |
SUENAGA Hitoshi Teikoku Chemical Industries, Fine Chemicals Development, Chief Investigator, 化成品部門, 研究部長
GAMOH Keiji Kochi University, Faculty of Education, Department of Chemistry, Associate Professor, 教育学部, 助教授 (90204817)
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| Project Period (FY) |
1997 – 1999
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| Keywords | Michael Addition Reaction / Nitrogen Heterocycles / Quinazoline Derivatives / Silica Gel Supports / Natural Products Synthesis / Chiral Columns / Epoxide Opening Reaction / High Pressure Condensation |
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| Research Abstract |
(a) Michael Addition Reactions of β-Ketoesters : Michael addition reactions of β-ketoesters with a variety of α, β-unsaturated carbonyl compounds using Yb(OTf)ィイD23ィエD2 / SiOィイD22ィエD2 or TfOH under solvent-free conditions have been established. In addition, homo-Michael addition reaction using activated cyclopropane derivatives has been achieved at high pressure.
(b) Asymmetric Catalysis Using Novel Nitrogen Heterocycles : Several chiral dipyridine and dithiophene derived ligands for the use in the catalytic enantioselective alkylation have been developed.
(c) Synthesis of Quinazoline Compounds : A variety of quinazoline derivatives have been prepared by condensation of cyano- and nitro-activated o-fluorobenzaldehydes with amidines in good yields.
(d) Supported Reactions on Silica Gel : Solvent-free organic reactions on silica gel supports have been developed: transformation of epoxides to halohydrins using LiX / SiOィイD22ィエD2 and chemoselective deprotection of N-Boc carboxamides using Yb(OTf)ィイD23ィエD2/ SiOィイD22ィエD2.
(e) Natural Product Synthesis : An enantioselective total synthesis of AI-77-B, a gastroprotective substance isolated from a culture broth of Bacillus pumilus AI-77, has been performed in high overall yield.
(f) Molecular Template Formation Using High Pressure Technique : Molecular template formation of bovine serum albumin-silica gels under high pressure conditions and its use for chiral HPLC analysis have been performed.
(g) Functional Group Transfonnations : Chemoselective reductive transformation of azides to N-Boc protected amines , Sc(OTf)ィイD23ィエD2- or TfOH-catalyzed Baeyer-Villiger oxidation and high-pressure-promoted LiClO)ィイD24ィエD2 -catalyzed reaction of epoxides with furans or thiophenes .
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