Development of Novel Carbon-Carbon Bond Forming Reactions Using Zirconocene Complex
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- ITO Hisanaka
- <i>School of Life Science, Tokyo University of Pharmacy and Life Science</i>
Bibliographic Information
- Other Title
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- ジルコノセン錯体を用いた新規炭素-炭素結合形成反応の開発
- ジルコノセン サクタイ オ モチイタ シンキ タンソ タンソ ケツゴウ ケイセイ ハンノウ ノ カイハツ
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Abstract
Novel zirconium-mediated carbon-carbon bond-forming reactions were developed. The allylic, γ-alkoxyallylic, allenyl, and γ,γ-dialkoxyallylic zirconium species can be prepared from corresponding ethers under mild conditions through the addition of a zirconocene-butene complex to the carbon-carbon multiple bond of the ethers and subsequent β-elimination of the alkoxyl group. The γ,γ-dialkoxyallylic zirconium species reacts with carbonyl compounds at the β-position of the zirconium atom like a ketene dialkyl acetal in the presence of stoichiometric amounts of Lewis acid and gave cyclopropane and/or cyclobutane derivatives. Intramolecular reaction of allylic zirconium species with acetal also develops as a ring contraction reaction of carbohydrates and morpholine derivatives. This method is useful for the construction of chiral highly functionalized carbocycles and pyrrolidines. The intramolecular ester transfer reaction through the zirconium-mediated coupling reaction of alkenyl carbamates gave γ-aminobutyric acid derivatives and pyrrolidine-3-carboxylic acids.<br>
Journal
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- YAKUGAKU ZASSHI
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YAKUGAKU ZASSHI 123 (11), 933-948, 2003-11-01
The Pharmaceutical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282681105630976
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- NII Article ID
- 110003614857
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- NII Book ID
- AN00284903
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- ISSN
- 13475231
- 00316903
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- NDL BIB ID
- 6745444
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- PubMed
- 14631755
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed