2004 Fiscal Year Final Research Report Summary
Enantioresolution of Alcohols and its Application to Organic Synthesis
| Project/Area Number |
14540552
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
分離・精製・検出法
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| Research Institution | Tohoku University |
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Principal Investigator |
WATANABE Masataka Tohoku University, Institute of Multidisciplinary Research for Advanced Materials, Associate Professor, 多元物資科学研究所, 助教授 (10006330)
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| Co-Investigator(Kenkyū-buntansha) |
KUWAHARA Shunsuke Tohoku University, Institute of Multidisciplinary Research for Advanced Materials, Research Associate, 多元物資科学研究所, 助手 (40359550)
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| Project Period (FY) |
2002 – 2004
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| Keywords | (S)-(+)-MαNP Acid / aryl methanol / diary methanol / 4-butylphthalide / matsutakeol / alcohols with aliphatic long-chain / enantioresolution / asymmetric synthesis |
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| Research Abstract |
(S)-(+)-2-Methoxy-2-(1-naphthyl)propionic acid so-called (S)-(+)-MαNP Acid, which was devised together by Professor Nobuyuki Harada, Dr shunsike Kuwahara and myself, has two roles ; one is diastereomeric separation of secondary alcohols and the other is simultaneous determination of absolute configuration of the hydroxyl group of the alcohols. We have paid our attention to these roles of our new chiral auxiliary, and reported syntheses of variety kinds of optical active aryl methanol and diary methanol, using the chiral auxiliary. We also focused on 4-butylphthalide known as a major fragrance of celery oil determined whose research started in 1890's. The absolute configuration of 4-butylphthalide has been speculated by the mechanism of asymmetric synthesis. The structure of the fragrance was finally determined as (S)-(-)-4-butylphthalide. We also succeeded in the synthesis of two enantiomers of the fragrance of matsutake mushroom known as "matsutakeol".
It is well known that enantioresolution of alcohols with aliphatic long-chaine and the determination of absolute configuration of the hydroxyl groups is difficult. There has been also no report of asymmetric synthesis of such alcohols. We, recently, succeeded in the enantioresolution of such alcohols with 36 carbons prepared from oleic acid and determination of absolute configuration of its hydroxyl group. This is a promising methodology to synthesis of biological active alcohols consists of long-chain aliphatic substituents.
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Research Products
(41 results)
