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首页> 外文期刊>Chemistry: A European journal >Rh~I-Catalyzed Regio- and Stereospecific Carbonylation of 1-(1-Alkynyl)cyclopropyl Ketones: A Modular Entry to Highly Substituted 5,6-Dihydrocyclopenta[c]furan-4-ones
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Rh~I-Catalyzed Regio- and Stereospecific Carbonylation of 1-(1-Alkynyl)cyclopropyl Ketones: A Modular Entry to Highly Substituted 5,6-Dihydrocyclopenta[c]furan-4-ones

机译：Rh〜I催化的1-（1-炔基）环丙基酮的区域和立体特异性羰基化：高度取代的5,6-二氢环戊五[c]呋喃-4-酮的模块化进入

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摘要

The rich appearance of highly substituted furans as key structural units in many bioactive natural products and important pharmaceuticals, and general application as versatile building blocks in organic synthesis have stimulated many efforts in exploration of novel methodology.[1, 2] Most recently, much attention has been paid on the development of metal-catalyzed transformations, including the cyclization of allenyl ketones,[3] 3-alkyn-1-ones,[3, 4] (Z)-2-en-4-yn-1-ols[5] and 2-(1-alkynyl)-2-alken-1-ones[6] or cycloisomerization of alkylidenecyclopropyl ketones[7]/cyclopropenyl ketones.[8] Very recently, 1-(1-alkynyl)-cyclopropyl ketones have been successfully developed by Schmalz[9a] and Zhang[9b–c] as readily available substrates for efficient construction of highly substituted furans and other cyclic compounds under the catalysis of gold(I) complexes (Scheme 1). Our continued effort to explore new reactions for synthesis of tetrasubstituted furans with high efficiency,[6e] has led us to target 3,4- fused bicyclic tetrasubstituted furans[10] as product for investigation. We envisaged that 1-(1-alkynyl)-cyclopropyl ketones might undergo some interesting transformation initiated by the rhodium(I)-catalyzed activation of the carbon- carbon s bond of cyclopropane ring.[11] Herein we wish to report our recent result that rhodium(I)-catalyzed a highly regioselective and stereospecific carbonylation reaction of 1-(1-alkynyl)-cyclopropyl ketones to afford 1,3,5-tri- or 1,3,5,6- tetrasubstituted 5,6-dihydro-cyclopenta[c]furan-4-ones[12] initiated by the activation of the carbon-carbon s bond.
机译：在许多生物活性天然产物和重要药物中，高度取代的呋喃作为主要结构单元的丰富外观以及在有机合成中作为通用构件的普遍应用激发了许多探索新方法的努力。[1，2]最近，备受关注。已经在金属催化转化的发展方面付出了很多努力，包括烯丙基酮，[3] 3-炔-1-酮，[3，4]（Z）-2-en-4-yn-1-ols的环化[5]和2-（1-炔基）-2-链烯-1-酮[6]或亚烷基环丙基[7] /环丙烯基酮的环异构化。[8]最近，Schmalz [9a]和Zhang [9b–c]成功开发了1-（1-炔基）-环丙基酮作为可轻易获得的底物，用于在金催化下高效构建高度取代的呋喃和其他环状化合物。 I）复合物（方案1）。我们不断努力探索高效合成四取代呋喃的新方法，[6e]使我们以3,4-稠合双环四取代呋喃[10]为研究目标。我们设想1-（1-炔基）-环丙基酮可能会受到铑（I）催化的环丙烷环碳-碳键活化的影响而引发一些有趣的转变。[11]在此，我们希望报告我们最近的结果，即铑（I）催化1-（1-炔基）-环丙基酮的高度区域选择性和立体选择性羰基化反应，从而得到1,3,5-三-或1,3,5，通过碳-碳s键的活化引发的6-四取代的5,6-二氢-环戊基[c]呋喃-4-酮[12]。

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