Nickel/Zinc Chloride-Promoted Domino Reaction of polyenynes
| Project/Area Number |
16590010
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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 |
Chemical pharmacy
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| Research Institution | Nagoya City University |
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Principal Investigator |
IKEDA Shin-ichi Nagoya City University, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究科, 助教授 (90254309)
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| Project Period (FY) |
2004 – 2005
|
| Project Status |
Completed (Fiscal Year 2005)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2005: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2004: ¥2,100,000 (Direct Cost: ¥2,100,000)
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| Keywords | nickel / zinc chloride / enone / dienyne / domino process |
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| Research Abstract |
A Ni(0)/ZnCl_2 system effectively promotes the coupling of enones and alkene-tethered alkynes. In the reaction with 1,6-enynes, the oxidative cyclization of Ni(0) species on enones across the alkyne part followed by ZnCl_2-promoted cleavage generates alkenylnickel intermediates. Subsequent migratory insertion of the tethered alkene occurs with 5-exo-cyclization. When the resulting alkylnickel intermediates have β-hydrogen atoms, the reaction terminates by β-hydrogen elimination to provide cyclopentane derivatives. On the other hand, an alkylnickel intermediate that does not have β-hydrogen atoms undergoes the insertion of a second alkene unit to cause a domino effect via a three-fold C-C bond formation process.
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Report
(3 results)
Research Products
(4 results)
