Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: An analysis of the factors controlling stereoselectivity
Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: An analysis of the factors controlling stereoselectivity
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DOI：
10.1021/jo060077r
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发表时间：
2006-07-07
影响因子：
3.6
通讯作者：
Woerpel, K. A.
中科院分区：
文献类型：
--
作者：
Billings, Susan B.;Woerpel, K. A.
[图形]在C - 2位被噻吩基（以及其他杂原子）取代的环己酮缩醛的反应表明，这些取代基对亲核取代反应的立体选择性具有强大的影响。这些反应的反式选择性与相应酮的行为相关。这些实验支持了这样一种可能性，即通过氧鎓离子进行的缩醛反应是在费尔金 - 安（Felkin - Anh）控制下进行的。
[GRAPHICS]The reactions of cyclohexanone acetals substituted with thiophenyl groups ( and other heteroatoms) at C-2 demonstrate the powerful influence that these substituents have on the stereoselectivity of nucleophilic substitution reactions. The trans selectivities of these reactions correlate with the behavior of the corresponding ketones. These experiments lend support to the possibility that the reactions of the acetals, which proceed via oxocarbenium ions, are operating under Felkin-Anh control.