| Project/Area Number |
62550623
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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 |
Synthetic chemistry
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
SATO Fumie Tokyo Institute of Technology, Faculty of Engineering, Professor, 工学部, 教授 (50016606)
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| Co-Investigator(Kenkyū-buntansha) |
KOBAYASHI Yuichi Tokyo Institute of Technology, Faculty of Engineering, Associate Professor, 工学部, 助教授 (90153650)
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| Project Period (FY) |
1987 – 1989
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| Project Status |
Completed (Fiscal Year 1989)
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| Budget Amount *help |
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1989: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1988: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1987: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | Sharpless reagent / allylic alcohols / furanyl alcohols / thienyl alcohols / 1, 2-diastereoselective / 不斉酸化 / 1、2-不斉誘導 / 生理活性化合物 / 不斉合成 / エノラ-ト / プロピオン酸エステル / 4級炭素 / アミノアルコール / α-N、N-ジベンジルアミノフロパナール / 1、2-不斉誘導反応 / 1, 2不斉誘導反応 / 不斉エポキシ化反応 / 1, 2-ジオール / β-アミノアルコール / β-ハロゲノアルコール / α-アミノアルデヒド / α-アミノケトン |
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| Research Abstract |
We have found that the kinetic resolution of allylic alcohols possessing a heteroatom substituent at gamma-position by using the Sharpless reagent proceeds with very large rate differences for the two enantismers. We also found that the kinetic resolution of 2-furanyl alcohols and 2-thienyl alcohols also proceeds efficiently thus providing a general method for preparation of homochiral 2-furanyl alcohols and 2-thienyl alcohols, respectively.
With highly efficient method for preparation of these secondary alcohols in hand, we have devoted our efforts to use these alcohols for preparation of natural products and important intermediates for synthesis of biological importance by using 1,2-diastereoselective induction reactions and use of the reactivity of the heteroatom substituents, and furyl and thienyl moiety. As a result, we have succeeded to prepare alpha-hydroxy carboxylic acids, vinyl epoxides, 1-vinyl-1,2-diols, alpha,beta-dialkoxy aldehydes, and gamma-lactones in chiral forms.
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