Control of planar, axial and helical chiralities based on the asymmetric ring-closing metathesis
| Project/Area Number |
24550121
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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 | Osaka Prefecture University |
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Principal Investigator |
Kamikawa Ken 大阪府立大学, 理学(系)研究科(研究院), 教授 (40316021)
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| Project Period (FY) |
2012-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2013: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
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| Keywords | asymmetric synthesis / 有機化学 / 面不斉 / 軸不斉 / らせん不斉 / 不斉閉環メタセシス / クロム錯体 / 閉環メタセシス / 不斉配位子 |
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| Outline of Final Research Achievements |
The molybdenum-catalyzed asymmetric ring-closing metathesis (ARCM) of the various Cs-symmetric (π-arene)chromium substrates proceeded smoothly and the corresponding bridged planar-chiral (π-arene)chromium complexes were obtained in excellent yields with excellent enantioselectivity of up to >99% ee. With a proper substituent, such as N-indolyl or 1-naphthyl, at the 2-positions of the η6-1,3-diisopropenylbenzene ligands, both biarylic axial chirality and π-arene-based planar-chirality could be simultaneously induced in the ARCM products via the double desymmetrization. The axial chirality thus induced was retained even after the removal of the chromium-carbonyl fragment, and the metal-free axially chiral biaryl/heterobiaryl compounds were obtained in up to >99% ee with complete retention of the enantiomeric purity. The overall protocol presented in this report can be regarded as a novel method of catalytically preparing axially chiral heterobiaryls/biaryl
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Report
(5 results)
Research Products
(51 results)
