Developments in furan syntheses

Developments in furan syntheses
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DOI:
10.1002/anie.200461668
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发表时间:
2005-01-01
影响因子:
16.6
通讯作者:
Brown, RCD
Brown, RCD
中科院分区:
化学1区
文献类型:
--
作者:
Brown, RCD

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呋喃的合成已经吸引了超过世纪的巨大兴趣,[1]反映了这些杂环在天然和合成物质中的重要性[2]以及对其合成的更具选择性和通用性的方法的需求。特别是,发展的路线,使取代的呋喃在温和的条件下,从简单容易获得的起始材料的简易组装仍然是一个重要的objective.Classical方法取代的呋喃涉及的二羰基化合物或等价物的环缩合,或取代现有的呋喃环。[1]替代策略已经探索了含炔和丙二烯的化合物的环异构化(方案1)。[1a B,3,4]然而,存在一些限制,包括容易获得含有敏感官能团的丙二烯基底物和不能通过丙二烯的直接环异构化制备3,4-取代的呋喃。
The synthesis of furans has attracted tremendous interest for well over a century,[1] reflecting both the importance of these heterocycles in natural and synthetic substances [2] and the requirement for more selective and versatile approaches for their synthesis. In particular, the development of routes that allow the facile assembly of substituted furans under mild conditions from simple readily available starting materials remains an important objective.Classical approaches to substituted furans have involved the cyclocondensation of dicarbonyl compounds or equivalents, or the substitution of an existing furan ring.[1] Alternative strategies have explored the cycloisomerization of alkyne-and allene-containing compounds (Scheme 1).[1a, b, 3, 4] However, there are some limitations, including ease of access to allenyl substrates that contain sensitive functional groups and the inability to prepare 3, 4-substituted furans by the direct cycloisomerization of allenes.