| Project/Area Number |
61550620
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Osaka University |
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Principal Investigator |
HOSOKAWA Takahiro Faculty of Engineering Science,Osaka University, 基礎工学部, 助教授 (90029520)
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| Project Period (FY) |
1986 – 1987
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| Project Status |
Completed (Fiscal Year 1987)
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| Budget Amount *help |
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1987: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1986: ¥1,400,000 (Direct Cost: ¥1,400,000)
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| Keywords | Cyclic acetal / Palladium catalyst / Phenyl acetaldehyde / 1,3-propanediol / (R,R)-2,4-Pentanediol / 銅塩助触媒 / フロンタリン / Wacker型触媒 / 位置選択性 / Michael型付加物 / 光学活性フロンタリン |
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| Research Abstract |
In order to develope new types of synthetic reactions using transition metal catalysts, we have studied Pd(II)-catalyzed acetalization of olefins with diols or alcohols. Firstly, the acetalization of styrene was attempted to get phenyl acetaldehyde which is one of important starting materials for the preparation of medicines and perfumes. The acetalization with 1,3-propanediol or methanol by using a catalyst system of Pdcl_2-CuCl-O_2 was found to proceed regioselectively to give the precursor of desired product. Optically active cyclic acetals were then prepared from acrylic esters,acrylonitrile,and styrene by the same procedure with (R,R)-2,4-pentanediol. Vinyl ketones gave the procursor of benzoyl acetaldeyde as the sole product if Na_2HPO_4 was used as an additive. The <gamma>-position of <alpha>syanoallylic acetates was regioselectively acetalized under the normal conditions. The shortest synthesis of natural and unnatural fromtalin was performed via intramolecular acetalization of an optically active olefinic diol.
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