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Asymmetric Organocatalytic Domino Michael/Aldol Reactions: Enantioselective Synthesis of Chiral Cycloheptanones, Tetrahydrochromenones, and Polyfunctionalized Bicyclo[3.2.1]octanes


  • The authors acknowledge Evonik Degussa and the DFG (Priority Programme Organocatalysis) for financial support as well the Fonds der Chemischen Industrie for a stipend given to A.K.


C′mon 1,2-dione: A new diastereo- and enantioselective Lewis base catalyzed domino Michael/aldol reaction converts α,β-unsaturated aldehydes and 1,2-diones into chiral bicyclo[3.2.1]octane-6-carbaldehydes. The products are produced in good to excellent enantioselectivities (90–98 % ee) and can be transformed into bicyclic diols and triols. Additionally, a retro-aldol cyclization provides access to valuable tetrahydrochromenones (see scheme).

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