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

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

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...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (20), p.3699-3702
Hauptverfasser: Rueping, Magnus, Kuenkel, Alexander, Tato, Francisco, Bats, Jan W
Format: Artikel
Sprache:eng
Schlagworte:
aldol reaction
domino reaction
Michael addition
organocatalysis
prolinol ethers
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Zusammenfassung: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).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200900754