2001 Fiscal Year Final Research Report Summary
The developnent of New Synthetic Methods Based on Sulfoxide-Metal Exchange
| Project/Area Number |
11640545
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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 | Science Uhiversity of Tokyo |
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Principal Investigator |
TSUYOSHI Satoh Facility of Science, Science Uhiversity of Tokyo professor, 理学部, 教授 (20089329)
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| Project Period (FY) |
1999 – 2001
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| Keywords | carbanion / carbenoid / magnesium carbenoid / sulfoxide / cyclopentenone / enaminonitrile / allene / carboxylic acid |
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| Research Abstract |
1.The reaction of the sulfinylaziridines with a Griguard reagent gave the aziridinylmagnesiums. Cross coupling of this aziridinymagnesiumes with alkylhalides catalyzed by Cu(I) iodide gave the alkylated aziriHines, from which the asymmetric synthesis of act-disubstituted p-amiho acids was realized.
2.Addition of cyanomethyllithium to 1-chloroyinyl p-tolyl sulfoxides gave the cyclopentadiehyl enaininonitriles in high yields. A novel synthesis of optically active 4, 4-disubstituted cyclopentenone derivatives was established from the enaminonitriles.
3.A new synthesis of highly functionalized carboxylic acid derivatives was realized from 1-chlorovinyl p-tolyl sulfoxides and lithium enolate of acetic acid esters.
4.A new method for generation of magnesium cyclopropylidenes and a synthesis of alkylidenecyclopropanes was realized.
5.A new method for the synthesis ofallenes through the magnesium alkylidene carbenoids was established.
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