1999 Fiscal Year Final Research Report Summary
Steroselective Intramolecular Cyclization Using Palladium Catalyst and Its Application to the Synthesis of Natsural Products
| 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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| Keywords | stereoselective cyclization / palladium (II) catalyst / silver trifluoroacetate / trans(2,6)piperidine / trans(2,4)piperidine / (+)-prosopinine / (-)-SS20846A / (+)-Deoxymannojirimycin |
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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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Research Products
(7 results)
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[Publications] Hajime Yokoyama, Ryo Hydo, Akiko Nakada, Seiji, Yamaguchi, and Yoshiro Hirai, Tadashi Kometani, Michimasa Goto, Norio Shibata, and Yoshio Takeuchi: "Asymmetric Synthesis of Chiral 2-Fluorinated 1,3-Propanediols and Its Application to the Preparation of Monofluorinated Chiral Synthon"Tetrahedron Letters. 39. 7741-7744
Description
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