2010 Fiscal Year Final Research Report
Development of wide scope asymmetric dipolar cycloaddition reactions and its synthetic applications
| Project/Area Number |
20200052
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| Research Category |
Grant-in-Aid for Scientific Research on Innovative Areas (Research a proposed research project)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
Drug development chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
SUGA Hiroyuki Shinshu University, 工学部, 教授 (60211299)
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| Project Period (FY) |
2008 – 2010
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| Keywords | 不斉合成・反応 / 生物活性物質 / 1,3-双極子 / 付加環化 / キラルルイス酸 |
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| Research Abstract |
A generality for diazo substrates was widely expanded in the Lewis acid catalyzed asymmetric cycloaddition reactions of cyclic carbonyl ylides generated from diazo carbonyl compounds. For example, highly enantioselective cycloadditions of a cyclic carbonyl ylide generated from a diazo compound containing a pyrrolidine ring could be successfully applied to an asymmetric total synthesis of (+)-Tashiromine. High levels of asymmetric induction were also found to obtain in the similar asymmetric cycloaddition reactions of cyclic azomethine ylides generated from diazo imine derivatives. The chiral Ni(II) complexes originally developed in our laboratory was also found to be effective catalysts for a wide scope of use in asymmetric cycloaddition reactions of nitrile oxides, diazo esters, and cyclic ylides.
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[Journal Article] Inverse Electron Demand Asymmetric Cycloadditions of Cyclic Carbonyl Ylides Catalyzed by Chiral Lewis Acids-Scope and Limitations of Diazo and Olefinic Substrates2010
Author(s)
Hiroyuki SUGA, Satoshi HIGUCHI, Motoo OHTSUKA, Daisuke ISHIMOTO, Tadashi ARIKAWA, Yuta HASHIMOTO, Shunta MISAWA, Teruko TSUCHIDA, Akikazu KAKEHI, Toshihide BABA
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Journal Title
Tetrahedron 66,(16)
Pages: 3070-3089
Peer Reviewed
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