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2010•Journal of the American Chemical SocietyRequires access

Desymmetrization of Cyclohexadienones via Brønsted Acid-Catalyzed Enantioselective Oxo-Michael Reaction

Qing Gu, Zi‐Qiang Rong, Chao Zheng, Shu‐Li You

Open publisher page 259 citations

Abstract

Desymmetrization of cyclohexadienones via enantioselective oxo-Michael reaction catalyzed by chiral phosphoric acid to afford highly enantioenriched 1,4-dioxane and tetrahydrofuran derivatives in excellent yields has been realized. The newly established methodology allows the facile enantioselective synthesis of cleroindicins C, D, and F.

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What this paper is about

Desymmetrization of cyclohexadienones via enantioselective oxo-Michael reaction catalyzed by chiral phosphoric acid to afford highly enantioenriched 1,4-dioxane and tetrahydrofuran derivatives in excellent yields has been realized. The newly established methodology allows the facile enantioselective synthesis of cleroindicins C, D, and F.

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Available abstract

Desymmetrization of cyclohexadienones via enantioselective oxo-Michael reaction catalyzed by chiral phosphoric acid to afford highly enantioenriched 1,4-dioxane and tetrahydrofuran derivatives in excellent yields has been realized. The newly established methodology allows the facile enantioselective synthesis of cleroindicins C, D, and F.

Key concepts: Desymmetrization, Enantioselective synthesis, Chemistry, Phosphoric acid, Catalysis, Tetrahydrofuran, Michael reaction, Brønsted–Lowry acid–base theory

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