2016 Fiscal Year Final Research Report
Novel cascade reactions triggered by silyl acetal activation
| Project/Area Number |
26460015
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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 |
Chemical pharmacy
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| Research Institution | Tokyo University of Pharmacy and Life Science |
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Principal Investigator |
Yanai Hikaru 東京薬科大学, 薬学部, 准教授 (10408685)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | 有機化学 / シリルアセタール / ブレンステッド酸 / 多環式芳香族化合物 / カスケード反応 |
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| Outline of Final Research Achievements |
By using our own acid catalysts, we recently found that some silyl acetals were easily formed. On the basis of this finding, we developed some novel cascade reactions induced by treatment of the silyl acetals with fluoride sources. In particular, silyl acetals derived from 4-alkynylisocoumarine derivatives produced 1,2,3,4-tetrasubstitued naphthalenes in a highly regioselective manner.
Our naphthalene synthesis is the two-step reaction; 1) acidic zwitterion-induced addition of ketene silyl acetal to lactonic carbonyl group, and 2) fluoride-triggered ring-rearrangement reaction. In the first step, a notably high level of chemoselectivity was observed. This is an important advantage to realize a wide range of application scope for the present methodology.
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| Free Research Field |
有機化学
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