1997 Fiscal Year Final Research Report Summary
Development of palladium catalyzed-reaction and its synthetic application
| Project/Area Number |
07455441
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Kurashiki University of Science and the Arts |
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Principal Investigator |
MANDAI Tadakatsu Kurashiki Univ.of Science and the Arts.Department of Chemical Technology.professor, 産業科学技術学部, 教授 (80131621)
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| Project Period (FY) |
1995 – 1997
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| Keywords | palladium catalyst / propargylic carbonate / Carbonylation |
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| Research Abstract |
An allenic ester, produced by palladium-catalyzed carbonylation of a propargylic carbonate, provides a further synthetically useful transformation because of a reactive allenic SP carbon. To demonstrate the utility of the allenic ester, we designed a following domino-type carbonylation/Diels-Alder reaction sequence. Carbonylation of a propargylic carbonate having a vinyl group in place of acetylenic proton provides an alpha-vinyl allenic ester which can be recognized as an electron-defficient conjugated diene. This alpha-vinyl allenic ester undergoes intramolecular Diels-Alder reaction with a methyl enol ether as an electron-rich dienophile, affording an indene skeleton. This synthetically interesting reaction was applied to an efficient construction of vitamin D_3 intermediate.
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