Development of New Reactions for Carbon-Carbon Bond Formation by Using Carbocation Species.
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- Tanino Keiji
- Division of Chemistry, Graduate School of Science, Hokkaido University
Bibliographic Information
- Other Title
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- カルボカチオン活性種の設計を基盤とする炭素骨格構築法の開発
- カルボカチオン カッセイシュ ノ セッケイ オ キバン ト スル タンソ コッカク コウチクホウ ノ カイハツ
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Abstract
New synthetic methods for functionalized carbocyclic compounds were developed on the basis of [3 + 2] and [5 + 2] cycloaddition reactions by using carbocation species. Under the influence of a Lewis acid, 3- (methylthio) -2-siloxyallyl acetates reacted with various kinds of olefins to afford the corresponding cyclopentanones in good yields. The sterically more hindered regioisomer was predominantly formed in every case, and surprisingly high stereoselectivity was also observed in certain cases. An efficient synthetic method for (-) -coriolin has been developed on the basis of the [3 + 2] cycloaddition reaction. On the other hand, 5-acetoxy-2- [(trimethylsilyl) methyl] -1-penten-3-yne-dicobalthexacarbonyl underwent [5 + 2] cycloaddition reactions with enol triisopropylsill ethers to give seven-membered compounds. The reactions with cyclic enol silyl ethers as well as acyclic enol silyl ethers exhibited remarkably high diastereoselectivity.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 59 (6), 549-559, 2001
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282680253394944
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- NII Article ID
- 10012769060
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 5797585
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed