Rh-catalyzed [5+1] and [4+1] cycloaddition reactions of 1,4-enyne esters with CO: a shortcut to functionalized resorcinols and cyclopentenones |
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Authors: | Fukuyama Takahide Ohta Yuko Brancour Célia Miyagawa Kazusa Ryu Ilhyong Dhimane Anne-Lise Fensterbank Louis Malacria Max |
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Institution: | Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan. fukuyama@c.s.osakafu-u.ac.jp |
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Abstract: | We have developed novel Rh-catalyzed n+1]-type cycloadditions of 1,4-enyne esters, which involve an acyloxy migration as a key step. The efficient preparation of functionalized resorcinols, including biaryl derivatives, from readily available 1,4-enyne esters and CO was achieved by Rh-catalyzed 5+1] cycloaddition accompanied by 1,2-acyloxy migration. When enyne esters had an internal alkyne moiety, the reaction proceeded by a 4+1]-type cycloaddition involving 1,3-acyloxy migration, leading to cyclopentenones. |
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