Palladium-catalyzed stereospecific epoxide-opening reaction of gamma,delta-epoxy-alpha,beta-unsaturated esters with an alkylboronic acid leading to gamma,delta-vicinal diols with double inversion of the configuration |
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| Authors: | Hirai Atsushi Yu Xiao-Qiang Tonooka Terumichi Miyashita Masaaki |
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| Affiliation: | Division of Chemistry, Graduate School of Science, Hokkaido University, 060-0810 Sapporo, Japan. |
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| Abstract: | A palladium-catalyzed stereospecific epoxide-opening reaction of gamma,delta-epoxy-alpha,beta-unsaturated esters with an alkylboronic acid leading to gamma,delta-vicinal diols is described, which proceeds with retention of the configuration, i.e., via two consecutive S(N)2 processes, to afford the corresponding gamma,delta-cyclic boronates in high yields. |
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