Tandem carbon-carbon bond-forming radical addition-cyclization reaction of oxime ether and hydrazone.
Tandem carbon-carbon bond-forming radical addition-cyclization reaction of oxime ether and hydrazone.
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DOI：
10.1021/jo0341057
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发表时间：
2003-06
期刊：
影响因子：
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通讯作者：
H. Miyabe;Masafumi Ueda;K. Fujii;Azusa Nishimura;T. Naito*
中科院分区：
文献类型：
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作者：
H. Miyabe;Masafumi Ueda;K. Fujii;Azusa Nishimura;T. Naito*
介绍了一种新颖的肟醚和腙分子内与α，β-不饱和羰基相连的串联自由基加成-环化反应。肟醚1、2和4分别与丙烯酰基和甲基丙烯酰基连接，通过C-C键形成的串联过程，顺利地进行自由基反应生成杂环化合物。在Zn（OTf）（2）作为刘易斯酸存在下，腙5发生串联反应，得到反式环状产物17，而没有形成顺式异构体。研究了手性肟醚19的非对映选择性自由基加成-环合反应。19的串联反应在水介质中也能顺利进行，为不对称合成γ-丁内酯和β-氨基酸衍生物提供了新的方法。
The novel tandem radical addition-cyclization of oxime ethers and hydrazones intramolecularly connected with the alpha,beta-unsaturated carbonyl group is described. The radical reaction of oxime ethers 1, 2, and 4 connected with acryloyl and methacryloyl moieties proceeded smoothly to give the heterocycles via a tandem C-C bond-forming process. The tandem reaction of hydrazone 5 took place in the presence of Zn(OTf)(2) as a Lewis acid to give the trans-cyclic product 17 without the formation of the cis-isomer. The diastereoselective radical addition-cyclization reaction of chiral oxime ether 19 was also studied. The tandem reaction of 19 proceeded smoothly even in aqueous media, providing the novel method for asymmetric synthesis of gamma-butyrolactones and beta-amino acid derivatives.