| Project/Area Number |
24850005
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| Research Category |
Grant-in-Aid for Research Activity Start-up
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| Allocation Type | Single-year Grants |
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| Research Field |
Organic chemistry
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| Research Institution | The University of Tokyo |
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Principal Investigator |
HIRANO keiichi 東京大学, 薬学研究科(研究院), 助教 (40633392)
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| Project Period (FY) |
2012-08-31 – 2014-03-31
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| Keywords | 多置換オレフィン / アルキン / ジボリル化 / ホウ素アート錯体 / ジボロン / trans-ジボリル化 / 有機触媒 / 中性Lewis塩基 / パーフルオロアルキル化 / パーフルオロアリール化 / ハロゲンー金属交換反応 |
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| Research Abstract |
Development of highly efficient and regio-/stereoselective synthesis of tetrasubstituted olefins is one of important problems to be addressed in synthetic organic chemistry. We have developed the first highly trans-selective diborylation reaction of alkyne by designing a pseudo-intramolecular reaction between diboron and propargylic alcohol. By combining this diborylation methodology with Suzuki-Miyaura cross-coupling reaction, we demonstrated a straightforward and regio-controlled synthesis of a tetrasubsituted olefin in one pot.
Moreover, diborylated products derived from propargylic alcohols possess the 1,2-oxaborol-2(5H)-ol structure, which has been attracting much attention as a potent pharmacophore against mycosis and others. We believe that this methodology will contribute to providing diverse new oxaborolol compounds and discovering a new type of boron-containing therapeutics.
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