Catalytic asymmetric synthesis of dihydrobenzofuran neolignans using intramolecular C-H insertion reactions
| Project/Area Number |
26860001
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | Hokkaido University |
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Principal Investigator |
ITO Motoki 北海道大学, 薬学研究科(研究院), 助教 (30610919)
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| Project Period (FY) |
2014-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | 合成化学 / 不斉触媒反応 / ロジウム(II)錯体 / C-H挿入反応 / ネオリグナン |
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| Outline of Final Research Achievements |
(1)An asymmetric synthesis of (-)-maximol A, a trans-resveratorol dimer containing a dihydrobenzofuran ring, has been achieved by exploiting the chiral dirhodium(II) complex-catalyzed intremolecular C-H insertion reaction of a diaryldiazomethane. In this process, dirhodium(II) tetrakis[N-tetrafluorophthaloyl-tert-leucinate], Rh2(S-TFPTTL)4, a fluorinated analogue of Rh2(S-PTTL)4, provided a dihydrobenzofuran core structure with up to 96% ee.
(2)The first examples of catalytic asymmetric intramolecular 1,6-C-H insertion reactions of α-diazoesters and diaryldiazomethanes have been developed. With Rh2(S-PTTL)4, the C-H insertion proceeded with perfect cis selectivity and high levels of asymmetric induction.
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Report
(3 results)
Research Products
(13 results)
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[Presentation] Synthetic Studies of 18E-lyngbyaloside C2015
Author(s)
Takuro Suzuki, Fumiya Tanada, Motoki Ito, Masahiro Anada, Shigeki Matsunaga, Shunichi Hashimoto
Organizer
The 3rd International Symposium on AMBITIOUS LEADER’S PROGRAM Fostering Future Leaders to Open New Frontiers in Materials Science
Place of Presentation
鈴木章ホール（北海道札幌市）
Year and Date
2015-11-18
Related Report
Int'l Joint Research
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