Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations
Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations
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DOI：
10.1002/ejoc.200700681
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发表时间：
2007-12-01
影响因子：
2.8
通讯作者：
Tan, Wen-Fei
中科院分区：
文献类型：
--
作者：
Bew, Sean P.;El-Taeb, Gamila M. M.;Tan, Wen-Fei
以碘为电泳剂的3-炔基-1，2-二醇的5-内-地高环反应顺利进行，从而获得了相应的β-碘呋喃的优异产率。所需的前体可以通过许多不同的方法获得，特别是共轭烯炔的区域选择性双羟基化和α-羟基羰基上的乙酰基加成。最初的碘呋喃可以使用许多策略进行同源，从各种过渡金属催化的偶联到卤素-金属交换以及随后与亲电试剂的偶联。因此，总体而言，这种方法代表了一种灵活、相对简单和非常有效的方法来处理各种高度取代的呋喃。(C)Wiley-VCH Verlag GmbH&Co.KGaA，69451，德国温海姆)。
5-endo-dig cyclisations of 3-alkyne-1,2-diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding beta-iodofurans. The necessary precursors are available from a number of different approaches, notably regioselective bis-hydroxylation of conjugated enynes and the addition of acetylides to a-hydroxy carbonyl groups. The initial iodofurans can be homologated using a number of strategies, ranging from various transition metal-catalysed couplings to halogen-metal exchange and subsequent coupling with an electrophile. Hence, this method overall represents a flexible, relatively brief and very efficient approach to a variety of highly substituted furans. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).