| Project/Area Number |
10640514
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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 | Toyama University |
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Principal Investigator |
HIRAI Yoshiro Faculty of Science, Toyama University Professor, 理学部, 教授 (70111747)
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| Project Period (FY) |
1998 – 1999
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| Project Status |
Completed (Fiscal Year 1999)
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| Budget Amount *help |
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1999: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1998: ¥2,000,000 (Direct Cost: ¥2,000,000)
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| Keywords | stereoselective cyclization / palladium (II) catalyst / silver trifluoroacetate / trans(2,6)piperidine / trans(2,4)piperidine / (+)-prosopinine / (-)-SS20846A / (+)-Deoxymannojirimycin / パラジウム錯体 / 消化管運動抑制作用 / (S)-glycidol / 1-deoxymannojirimycin / グリコシダーゼ阻害作用 / アザ糖類 |
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| Research Abstract |
The intramolecular cyclization of the optically active urethanes containing allylic alkohol was effected by treatment with bis(acetonitrile)palladium (II) chloride to give the trans(2,6)piperidine system as a single diastereoisomer. During these transformations, the Pd (II) species are not reduced and thus the catalyst can recycle without its reoxidation. On the other hand, cyclization of the simillar substrate containing allylic chloride using silver trifluoroacetate in the presence of sodium hydride afforded the cis(2,6)piperidine system. Cyclization of other substrates using these transition metal complexes was also examined and simillar results were obtained.
The cyclo-adducts obtained were proved to be useful chiral building blocks by their conversion into (+)-prosopinine, (-)-SS20846A, (+)-Deoxymannojirimycin, and (-)-hydroxysedamine, respectively
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