Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines.
Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines.
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DOI：
10.1016/j.tetlet.2015.01.006
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发表时间：
2015-06-03
影响因子：
1.8
通讯作者：
Gevorgyan V
中科院分区：
文献类型：
--
作者：
Shiroodi RK;Vera CI;Dudnik AS;Gevorgyan V
本文报道了一种新的金催化的呋喃和吡咯的发散合成方法。该反应的区域化学结果取决于底物末端炔上的取代基。因此，在炔部分具有烷基和芳基取代基的底物通过迁移环化异构化反应产生2，3，5-取代的呋喃和吡咯。然而，它们的硅类似物能够经历导致2，3，4-取代杂环的双重迁移过程。
A novel gold-catalyzed divergent sysnthesis of furans and pyrroles employing readily available homopropargylic aldehydes and imines have been developed. The regiochemical outcome of this reaction is dependent on the substituent on the terminal alkyne of substrate. Thus, substrates possessing alkyl and aryl substituent at the alkyne moiety produce 2,3,5-substituted furans and pyrroles via a migratory cycloisomerizaton reaction. Whereas, their silicon analogues are capable to undergo a double migratory process leading to 2,3,4-substituted heterocycles.