Catalytic Asymmetric Synthesis of Heterocyclic Compounds Using Dinuclear Metal Complexes
| Project/Area Number |
21790001
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Hokkaido University |
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Principal Investigator |
ANADA Masahiro 北海道大学, 大学院・薬学研究院, 准教授 (90344473)
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| Project Period (FY) |
2009 – 2010
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| Project Status |
Completed (Fiscal Year 2010)
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| Budget Amount *help |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2009: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | 合成化学 / 不斉触媒反応 / ロジウム(II)錯体 / ルイス酸 / ヘテロDiels-Alder反応 / ジヒドロピラノン / 1, 3-オキサジナン-4-オン / モレキュラーシーブス / 向山マイケル反応 / 向山アルドール反応 / 向山Michael反応 |
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| Research Abstract |
(1) The first example of a chiral Lewis acid-catalyzed enantioselective hetero-Diels-Alder (HDA) reaction between 1-dimethylamino-3-silyloxy-1,3-butadiene (Rawal's diene) and aldehydes is described. The cycloaddition reaction under the influence of 1 mol % of dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh_2(S-BPTPI)_4, proceeded cleanly and gave, after treatment with acetyl chloride, the corresponding dihydropyranones in up to 99% ee.
(2) A new route to the diarylheptanoids diospongins A and B was developed. The key step is a novel, one-pot sequential Rh_2(S-BPTPI)_4-catalyzed enantioselective HDA/TMSOTf-catalyzed Mukaiyama-Michael reaction process.
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Report
(3 results)
Research Products
(27 results)
