2011 Fiscal Year Final Research Report
Sequential Isoprene Unit Elongation Reaction Based on Rearrangement Reaction
| Project/Area Number |
21550099
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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 |
Synthetic chemistry
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| Research Institution | Yokohama National University |
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Principal Investigator |
HONDA Kiyoshi 横浜国立大学, 環境情報研究院, 准教授 (60231578)
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| Project Period (FY) |
2009 – 2011
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| Keywords | 選択的合成 / 反応 |
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| Research Abstract |
Methodology of[3, 3] sigmatropic rearrangement via generation of the enammonium salt from quaternary ammonium salt, elimination and isomerization, followed by hydrolysis to give(E)-aldehyde in good yield, was found out. The present method can be carried out the tandem rearrangement/reduction to give the corresponding amine. Thus, treatment of quaternary ammonium salt with t^BuOK or NEt_3 in the presence of pic-Borane resulted in aza-Claisen rearrangement, followed by reduction to give(E)-amino alkene in good yield. It should be noted that the present reaction proceeds via tandem elimination/[3, 3]-rearrangement/reduction mechanism which involves an initial formation of ylide followed by the elimination to the enammonium salt and the[3, 3] rearrangement of the resultant salt affords the iminium salt which gives the allylic amine by hydride reduction.
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