| Project/Area Number |
15550035
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
SHIBATA Ikuya Osaka University, Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (10196420)
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| Project Period (FY) |
2003 – 2004
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| Project Status |
Completed (Fiscal Year 2004)
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| Budget Amount *help |
¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2004: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 2003: ¥2,000,000 (Direct Cost: ¥2,000,000)
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| Keywords | allyltantalum / allyltin / transmetallation / Imines / Indium hydride / Reductive aldol reaction / Chemoselective reaction / Stereoselective reaction |
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| Research Abstract |
Although allylation of imines is a representative method to give homoallylic amines, there are still limitations in the method. No effective methods of the allylation of imines derived from aliphatic aldehydes and N-aliphatic amines have been reported so far. We report the characteristic reactivity of allylic tantalums toward imines. High imine-selectivity over carbonyls was observed, and the allylation of low electrophilic imines was established. This is a superior methodology of allylation of imines compared with conventional ones in terms of wide applicability to imines.
Reductive aldol reaction using metal hydrides, enone and aldehydes in one portion is a valuable route to β-hydroxy ketones because of convenient one-pot method without steady synthesis of metal enolates. However, the reaction has been a difficult issue because aldehydes are more susceptible than enones to conventional metal hydrides. We report the most effective method in which the catalytic use of indium(III) bromide (InBr3) was permitted.
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