Stereoselective Preparation of Enol Silyl Ethers via Formation of Vinylcopper Species by Silyl Migration
| Project/Area Number |
23550118
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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 | Tokyo University of Agriculture and Technology |
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Principal Investigator |
TSUBOUCHI Akira 東京農工大学, 工学(系)研究科(研究院), 助教 (40272637)
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| Project Period (FY) |
2011 – 2013
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
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| Keywords | ケイ素転位 / エノールシリルエーテル / アルケニル銅 / シリカート / 三成分連結反応 / 銅エノラート / 共役付加 / クロスカップリング / 触媒反応 / 有機銅 |
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| Research Abstract |
In the present research, a mew synthetic methodology using multi-component coupling has been developed for stereoselective preparation of enol sily ethers. The process is based on the formation of vinyl copper species by the Brook-type silly migration from sp2 carbon to enolate oxygen as a key reaction. The stereochemistry of the enol silly ethers thus formed is controlled by the formation of the cyclic silicate intermediates. Thus, it was found that the three-component coupling of alpha, beta-unsaturated acylsilanes, the Gilman reagents (or the Grignard reagents / t-BuOCu), and organic halides produced disubstituted enol silyl ethers stereoselectively. The present method is different in concept to conventional methods which rely on stereoselective formation of enolates by deprotonation of ketones.
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Report
(4 results)
Research Products
(14 results)
