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 alpha,beta-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).
Rueping
Magnus
M
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen, Germany. magnus.rueping@rwth-aachen.de
Kuenkel
Alexander
A
Tato
Francisco
F
Bats
Jan W
JW