Organocatalytic synthesis of highly substituted furfuryl alcohols and amines.
Organocatalytic synthesis of highly substituted furfuryl alcohols and amines.
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DOI：
10.1002/anie.201207300
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发表时间：
2012-11
影响因子：
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通讯作者：
J. Clark;Alistair Boyer;A. Aimon;Paloma Engel García;D. Lindsay;Andrew D. F. Symington;Yves Danoy
中科院分区：
文献类型：
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作者：
J. Clark;Alistair Boyer;A. Aimon;Paloma Engel García;D. Lindsay;Andrew D. F. Symington;Yves Danoy
开发了一种简单的取代呋喃的有机催化合成方法。该方法的新特点包括使用简单的硫醚作为有机催化剂，在中性条件下形成呋喃，而不是传统合成中使用的阴离子或酸性条件，以及多功能硫叶立德的中间体，它有可能被各种亲电体直接拦截，而不是被质子化得到硫离子。该反应以广泛的底物和亲核试剂进行，以很好的产率得到高度修饰的呋喃。这个过程是温和的，可能会导致形成一个脆弱的、与生物相关的环氧呋喃基序。硫醚催化与其他有机催化过程的互补性使反应可以并入三组分多米诺骨牌序列。
A simple organocatalytic synthesis of substituted furans has been developed. The novel features of the procedure include the use of a simple thioether as the organocatalyst, the formation of a furan under neutral conditions rather than the anionic or acidic conditions employed in conventional syntheses, and the intermediacy of a versatile sulfonium ylide that has the potential to be intercepted directly by a variety of electrophiles rather than being protonated to give a sulfonium ion. The reaction proceeds with a wide range of substrates and nucleophiles to give highly decorated furans in good yield. The process is mild and can lead to the formation of a fragile, biologically-relevant epoxyfuran motif. The complementary nature of the thioether catalysis with other organocatalyzed processes has allowed the reaction to be incorporated into a three-component domino sequence.