Development of new asymmetric spirocyclization based on boron-zinc transmetallation strategy
| Project/Area Number |
17K05858
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Shizuoka University |
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Principal Investigator |
Hidemi Yoda 静岡大学, 工学部, 教授 (20201072)
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| Co-Investigator(Kenkyū-buntansha) |
高橋 雅樹 静岡大学, 工学部, 教授 (30313935)
仙石 哲也 静岡大学, 工学部, 准教授 (70451680)
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| Project Period (FY) |
2017-04-01 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | アミドアリルボロン酸エステル / スピロ環 / キラルアミノフェノール / 臭化マグネシウム / 亜鉛触媒 / 有機化学 / 不斉触媒反応 / スピロ化合物 |
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| Outline of Final Research Achievements |
We developed a new catalytic system that enables enantioselective tin-free allylation with the aid of a newly prepared β-amido functionalized allylboronate for nucleophilic addition to isatins. This system consisting of a catalytic amount of diethylzinc in the presence of a newly prepared chiral aminophenol afforded the respective products in excellent yields with remarkably high enantiopurities.
Hydroxylactams prepared from N-carbonylphthalimides and β-amide allylboronates underwent ring opening-asymmetric reclosure in the presence of catalytic amounts of MgBr2 and a chiral aminophenol to afford the desired lactones in excellent yields with high enantioselectivities.
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| Academic Significance and Societal Importance of the Research Achievements |
不斉炭素構築法のうち特に有力な手法とされ、近年も多数の論文が報告されているアリル化反応の、環境調和かつ多官能性分子の合成に耐えうる手法を実現した。加えて、分子合成（特に薬剤候補分子合成）において利用価値の高いカルボニル基を配した生成物を得ることに成功した。また、立体化学や構成元素の異なるスピロラクタムを複数調製し、それらの生物活性を調査することで、構造と活性の相関関係を明らかとした。
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Report
(4 results)
Research Products
(37 results)
