Transition-Metal-Free Superbase-Promoted Stereoselective α-Vinylation of Ketones with Arylacetylenes: A General Strategy for Synthesis of β,γ-Unsaturated Ketones

Boris A. Trofimov*, Elena Yu. Schmidt, Nadezhda V. Zorina, Elena V. Ivanova and Igor' A. Ushakov

*A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia, Email: boris_trofimovirioch.irk.ru

B. A. Trofimov, E. Y. Schmidt, N. V. Zorina, E. V. Ivanova, I. A. Ushakov, J. Org. Chem., 2012, 77, 6880-6886.

DOI: 10.1021/jo301005p

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Abstract

KOtBu/DMSO promoted α-vinylation of aliphatic, cycloaliphatic, and alkyl aromatic (heteroaromatic) ketones with diverse arylacetylenes enables the synthesis of various β,γ-unsaturated ketones of E configuration in very good yields.

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Key Words

alkenylation

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ID: J42-Y2012-2580