Abstract
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 retroaldol cyclization provides access to valuable tetrahydrochromenones (see scheme).
Original language | English (US) |
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Pages (from-to) | 3699-3702 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 48 |
Issue number | 20 |
DOIs | |
State | Published - May 4 2009 |
Externally published | Yes |
Keywords
- Aldol reaction
- Domino reaction
- Michael addition
- Organocatalysis
- Prolinol ethers
ASJC Scopus subject areas
- General Chemistry
- Catalysis