Novel Stereocontrolled Synthesisof Highly Functionalized Cyclobutanes by Epoxide Opening througha Carbanion Intermediate in Heteroconjugate Addition
Novel Stereocontrolled Synthesisof Highly Functionalized Cyclobutanes by Epoxide Opening througha Carbanion Intermediate in Heteroconjugate Addition
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DOI：
10.1055/s-0028-1088108
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发表时间：
2009-04
期刊：
影响因子：
2
通讯作者：
M. Adachi;E. Yamauchi;T. Komada;M. Isobe
中科院分区：
文献类型：
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作者：
M. Adachi;E. Yamauchi;T. Komada;M. Isobe
我们证明了反式-1，2-二取代环氧化物通过分子内碳负离子开环过程形成新的环丁烷环。在该反应中，亲核负碳离子不是通过α-质子夺取而是通过杂共轭加成生成的。这些研究表明，每个环氧化物（顺式和反式）的不同配置不影响其反应性和在环化步骤中的反应速度，提供多官能化的环丁烷在区域和立体定向的方式。
We have demonstrated a new cyclobutane ring formation from the trams-1,2-disubstituted epoxides through intramolecular carbanion opening process. In this reaction, the nucleophilic carbanion is generated not via α-proton abstraction but via heteroconjugate addition. These studies indicate that the different configuration of each epoxide (syn and anti) do not affect its reactivity and the reaction velocity in the cyclization step, providing multifunctionalized cyclobutanes in a regio- and stereospecific manner.