Organocatalytic, Highly Enantioselective Vinylogous Mukaiyama–Michael Reaction of Acyclic Dienol Silyl Ethers

Authors


  • We gratefully acknowledge generous financial support from the Deutsche Forschungsgemeinschaft (SCHN 441/10-1), the Deutscher Akademischer Austauschdienst for a predoctoral fellowship (V.G.), the Alexander von Humboldt Foundation for postdoctoral fellowships (S.S. und T.M.), and Evonik and Chemetall for chemicals.

Abstract

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Now also acyclic: The first catalytic, enantioselective, vinylogous Michael reaction of linear, acyclic dienol silyl ethers was achieved. The reaction, based upon the principle of iminium ion catalysis, delivered 1,7-dioxo compounds in one step with good yields, complete regio-, and excellent enantioselectivity. γ-Substituted dienol silyl ethers furnished products with two new stereogenic centers with good diastereoselectivity. Ms=mesityl, PNBA=para-nitrobenzoic acid.

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