1997 Fiscal Year Final Research Report Summary
Synthetic Study Using a New Active Reaction Species, Nitrosoketene
| Project/Area Number |
08672405
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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 |
Chemical pharmacy
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| Research Institution | Tohoku University |
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Principal Investigator |
KATAGIRI Nobuya Tohoku University, Faculty of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (60089787)
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| Co-Investigator(Kenkyū-buntansha) |
SUGIHARA Takumiti Tohoku University, Faculty of Pharmaceutical Sciences, Instructor, 薬学部, 助手 (40222054)
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| Project Period (FY) |
1996 – 1997
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| Keywords | nitrosoketene / FT-IR spectrum / cyclic nitrone / 1,3-dipolar cycloaddition / asymmetric synthesis / modified amino acid / isonitroso Meldrum's acid / cyclopentenylglycine |
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| Research Abstract |
Previously, we reported that heating of isonitroso Meldrum's acid with ketones in a aprotic solvent to give cyclic nitrones. This reaction involves the 1,3-cycloaddition of ketone with nitrosoketene derived from isonitroso Meldrum's acid. In this research project, we synthesized chiral cyclic nitrones from the reaction of nitrosoketene with various chiral ketones, and achieved the asymmetric synthesis of modified amino acids via asymmetric 1,3-dipolar cycloaddition of the nitrones. Thus, reaction of nitrosoketene with (+)-nopinone or (+)-camphenilone gave a chiral nitrone as a single isomer whereas l-menthone reacted with nitrosokene to give two isomers of chiral nitrones. One of these isomers was used for the EPC synthesis of modified amino acids such as allylglycine and cyclopentenylglycine. Furthermore, we first succeeded the detection of nitrosoketene using FT-IR spectroscopy under collaboration with American researchers. Thus, we found that nitrosoketene was gradually generated from isonitroso Meldrum's acid above 80ﾟC and then decomposed about 160ﾟC,and that life time of nitrosoketene was 4 h at 90ﾟC.
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