Stereoselective synthesis of trisubstituted E-iodoalkenes by indium-catalyzed syn-addition of 1,3-dicarbonyl compounds to 1-iodoalkynes |
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Authors: | Tsuji Hayato Fujimoto Taisuke Endo Kohei Nakamura Masaharu Nakamura Eiichi |
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Institution: | Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. |
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Abstract: | Indium-catalyzed addition of 1,3-dicarbonyl compounds to 1-iodo-1-alkynes takes place exclusively in a syn-fashion to produce E-iodoalkenes. The iodine atom serves both as an activating group and as a group that controls the regioselectivity of the addition. The E-alkenyl iodide product can be further derivatized using either a one-pot or a two-pot procedure into trisubstituted olefins in high overall yield with retention of the stereochemistry. |
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