2,3,4-或2,3,5-三取代呋喃：环丙烯基酮的催化剂控制的高度区域选择性开环环异构化反应
2,3,4- or 2,3,5-trisubstituted furans: catalyst-controlled highly regioselective ring-opening cycloisomerization reaction of cyclopropenyl ketones.
作者信息
Ma Shengming, Zhang Junliang
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P R China.
出版信息
J Am Chem Soc. 2003 Oct 15;125(41):12386-7. doi: 10.1021/ja036616g.
2,3,4- or 2,3,5-trisubstituted furans were highly regioselectively formed from the cycloisomerization reaction of the same starting cyclopropenes 1 via the subtle choice of the transition metal halides. Under the catalysis of 5 mol % PdCl2(CH3CN)2, 2,3,5-trisubstituted furans 2 were given in 50-88% yields with 95-99% regioselectivities, while 2,3,4-trisubstituted furans 3 were formed in 78-96% yields with 99% regioselectivities under the catalysis of 5 mol % CuI.
通过对过渡金属卤化物的巧妙选择，由相同的起始环丙烯1经环异构化反应可高度区域选择性地生成2,3,4 - 或2,3,5 - 三取代呋喃。在5 mol% PdCl2(CH3CN)2催化下，可得到产率为50 - 88%、区域选择性为95 - 99%的2,3,5 - 三取代呋喃2；而在5 mol% CuI催化下，可生成产率为78 - 96%、区域选择性为99%的2,3,4 - 三取代呋喃3。
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