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Synfacts 2008(6): 0618-0618  
DOI: 10.1055/s-2008-1078392
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Indium-Catalyzed syn-Addition of 1,3-Dicarbonyl Compounds

Contributor(s): Mark Lautens, Praew Thansandote
H. Tsuji, T. Fujimoto, K. Endo, M. Nakamura, E. Nakamura*
The University of Tokyo, Japan
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Publikationsdatum:
21. Mai 2008 (online)

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Significance

An indium-catalyzed syn-addition of 1,3-dicarbonyl compounds and 1-iodo-1-alkynes gives exclusively E-iodoalkenes in good yields for a variety of dicarbonyls and alkynes. The vinyl iodide that is formed can be further functionalized using a Sonogashira or a Suzuki coupling in a one-pot or two-pot procedure.