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Stereoselective Synthesis of Trisubstituted E-Iodoalkenes by Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes

Hayato Tsuji, Taisuke Fujimoto, Kohei Endo, Masaharu Nakamura and Eiichi Nakamura*

*Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: nakamurachem.s.u-tokyo.ac.jp

H. Tsuji, T. Fujimoto, K. Endo, M. Nakamura, E. Nakamura, Org. Lett., 2008, 10, 1219-1221.

DOI: 10.1021/ol800105r


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Abstract

Indium-catalyzed addition of 1,3-dicarbonyl compounds to 1-iodo-1-alkynes produces exclusively 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 into trisubstituted olefins in high overall yield with retention of the stereochemistry.

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Indium-Catalyzed 2-Alkenylation of 1,3-Dicarbonyl Compounds with Unactivated Alkynes

K. Endo, T. Hatakeyama, M. Nakamura, E. Nakamura, J. Am. Chem. Soc., 2007, 129, 5264-5271.

Indium Triflate-Catalyzed Vinylation of β-Ketoesters with Acetylene Gas

M. Nakamura, K. Endo, E. Nakamura, Org. Lett., 2005, 7, 3279-3281.


Key Words

Active Methylenes


ID: J54-Y2008-0740